# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
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data_avk14f5
_database_code_depnum_ccdc_archive 'CCDC 1888875'
loop_
_audit_author_name
_audit_author_address
'Boris Averkiev'
;New Mexico Highlands University
United States of America
;
_audit_update_record
;
2019-01-08 deposited with the CCDC. 2019-10-14 downloaded from the CCDC.
;
_audit_creation_date 2018-07-27
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2018/1
_chemical_name_common ?
_chemical_name_systematic 3-phenylpyrrolidine-2,5-dione
_chemical_formula_moiety 'C10 H9 N O2'
_chemical_formula_sum 'C10 H9 N O2'
_chemical_formula_weight 175.18
_chemical_melting_point 349.8
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 9.285(5)
_cell_length_b 10.118(5)
_cell_length_c 15.913(8)
_cell_angle_alpha 80.568(6)
_cell_angle_beta 81.516(6)
_cell_angle_gamma 65.604(6)
_cell_volume 1337.8(11)
_cell_formula_units_Z 6
_cell_measurement_reflns_used 5654
_cell_measurement_temperature 100(2)
_cell_measurement_theta_max 30.30
_cell_measurement_theta_min 2.45
_shelx_estimated_absorpt_T_max 0.991
_shelx_estimated_absorpt_T_min 0.982
_exptl_absorpt_coefficient_mu 0.092
_exptl_absorpt_correction_T_max 0.7461
_exptl_absorpt_correction_T_min 0.6404
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1104 before and 0.0440 after correction.
The Ratio of minimum to maximum transmission is 0.8583.
The \l/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.305
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plate
_exptl_crystal_F_000 552
_exptl_crystal_size_max 0.2
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.1
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0352
_diffrn_reflns_av_unetI/netI 0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_number 19911
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 30.722
_diffrn_reflns_theta_min 2.225
_diffrn_ambient_temperature 100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed tube'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 5607
_reflns_number_total 8123
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection 'Bruker APEX2'
_computing_data_reduction 'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXL (Sheldrick, 2008)'
_refine_diff_density_max 0.381
_refine_diff_density_min -0.241
_refine_diff_density_rms 0.047
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.030
_refine_ls_hydrogen_treatment refall
_refine_ls_matrix_type full
_refine_ls_number_parameters 460
_refine_ls_number_reflns 8123
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0762
_refine_ls_R_factor_gt 0.0470
_refine_ls_restrained_S_all 1.030
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.1977P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1132
_refine_ls_wR_factor_ref 0.1299
_refine_special_details ?
_olex2_refinement_description
;
;
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary difmap
_atom_sites_solution_secondary difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.34061(13) 0.62623(14) 0.23887(7) 0.0511(3) Uani 1 1 d . . . . .
O2A O 0.69983(11) 0.43005(11) 0.01898(6) 0.0341(2) Uani 1 1 d . . . . .
N1A N 0.49645(13) 0.53849(12) 0.11771(7) 0.0283(2) Uani 1 1 d . . . . .
H1A H 0.419(2) 0.561(2) 0.0832(13) 0.058(5) Uiso 1 1 d . . . . .
C1A C 0.47074(16) 0.56944(14) 0.20241(9) 0.0315(3) Uani 1 1 d . . . . .
C2A C 0.63304(16) 0.52409(14) 0.23429(8) 0.0286(3) Uani 1 1 d . . . . .
H2A H 0.6470(18) 0.6144(17) 0.2290(10) 0.034(4) Uiso 1 1 d . . . . .
C3A C 0.74856(15) 0.43213(15) 0.16572(8) 0.0292(3) Uani 1 1 d . . . . .
H3AA H 0.7824(19) 0.3264(18) 0.1852(10) 0.037(4) Uiso 1 1 d . . . . .
H3AB H 0.838(2) 0.4542(19) 0.1483(11) 0.047(5) Uiso 1 1 d . . . . .
C4A C 0.65182(15) 0.46357(13) 0.09180(8) 0.0255(2) Uani 1 1 d . . . . .
C5A C 0.64838(15) 0.45236(14) 0.32567(8) 0.0292(3) Uani 1 1 d . . . . .
C6A C 0.68269(16) 0.51717(15) 0.38609(9) 0.0332(3) Uani 1 1 d . . . . .
H6A H 0.6897(19) 0.6123(18) 0.3707(10) 0.041(4) Uiso 1 1 d . . . . .
C7A C 0.70120(18) 0.45064(18) 0.46981(10) 0.0414(3) Uani 1 1 d . . . . .
H7A H 0.722(2) 0.500(2) 0.5123(12) 0.054(5) Uiso 1 1 d . . . . .
C8A C 0.68719(19) 0.31884(19) 0.49310(10) 0.0465(4) Uani 1 1 d . . . . .
H8A H 0.697(2) 0.276(2) 0.5532(13) 0.056(5) Uiso 1 1 d . . . . .
C9A C 0.6540(2) 0.25295(19) 0.43337(11) 0.0486(4) Uani 1 1 d . . . . .
H9A H 0.643(2) 0.157(2) 0.4471(13) 0.067(6) Uiso 1 1 d . . . . .
C10A C 0.6334(2) 0.31938(17) 0.34968(10) 0.0410(3) Uani 1 1 d . . . . .
H10A H 0.608(2) 0.269(2) 0.3050(12) 0.056(5) Uiso 1 1 d . . . . .
O1B O 1.04658(13) 0.37878(11) -0.15909(7) 0.0417(3) Uani 1 1 d . . . . .
O2B O 0.83447(11) 0.05003(11) -0.04382(6) 0.0361(2) Uani 1 1 d . . . . .
N1B N 0.93033(13) 0.22863(12) -0.08544(7) 0.0280(2) Uani 1 1 d . . . . .
H1B H 0.8676(19) 0.2889(18) -0.0490(10) 0.035(4) Uiso 1 1 d . . . . .
C1B C 1.03721(15) 0.26126(14) -0.14650(8) 0.0279(3) Uani 1 1 d . . . . .
C2B C 1.13773(14) 0.12375(13) -0.18926(8) 0.0263(2) Uani 1 1 d . . . . .
H2B H 1.2392(18) 0.0818(16) -0.1590(9) 0.031(4) Uiso 1 1 d . . . . .
C3B C 1.04640(17) 0.02423(15) -0.15988(9) 0.0311(3) Uani 1 1 d . . . . .
H3BA H 1.118(2) -0.077(2) -0.1362(11) 0.051(5) Uiso 1 1 d . . . . .
H3BB H 0.9902(19) 0.0209(17) -0.2050(11) 0.040(4) Uiso 1 1 d . . . . .
C4B C 0.92512(14) 0.09676(14) -0.08965(8) 0.0267(3) Uani 1 1 d . . . . .
C5B C 1.17641(15) 0.14984(14) -0.28467(8) 0.0286(3) Uani 1 1 d . . . . .
C6B C 1.33251(16) 0.08483(15) -0.31973(9) 0.0324(3) Uani 1 1 d . . . . .
H6B H 1.4135(19) 0.0245(17) -0.2818(10) 0.034(4) Uiso 1 1 d . . . . .
C7B C 1.37176(19) 0.10546(17) -0.40717(10) 0.0396(3) Uani 1 1 d . . . . .
H7B H 1.486(2) 0.0583(19) -0.4312(11) 0.048(5) Uiso 1 1 d . . . . .
C8B C 1.2552(2) 0.19022(19) -0.46062(10) 0.0443(4) Uani 1 1 d . . . . .
H8B H 1.283(2) 0.2087(19) -0.5216(12) 0.051(5) Uiso 1 1 d . . . . .
C9B C 1.0991(2) 0.2550(2) -0.42636(11) 0.0510(4) Uani 1 1 d . . . . .
H9B H 1.015(3) 0.321(2) -0.4600(13) 0.067(6) Uiso 1 1 d . . . . .
C10B C 1.05959(18) 0.23583(19) -0.33884(10) 0.0433(4) Uani 1 1 d . . . . .
H10B H 0.950(2) 0.2865(19) -0.3161(11) 0.047(5) Uiso 1 1 d . . . . .
O1C O 0.55806(11) 0.20935(11) 0.16533(6) 0.0353(2) Uani 1 1 d . . . . .
O2C O 0.39810(13) 0.17567(13) -0.08457(7) 0.0456(3) Uani 1 1 d . . . . .
N1C N 0.50971(13) 0.18303(12) 0.03318(7) 0.0283(2) Uani 1 1 d . . . . .
H1C H 0.614(2) 0.146(2) 0.0129(12) 0.055(5) Uiso 1 1 d . . . . .
C1C C 0.46577(14) 0.21915(13) 0.11549(8) 0.0262(2) Uani 1 1 d . . . . .
C2C C 0.28483(14) 0.27477(13) 0.13129(8) 0.0268(3) Uani 1 1 d . . . . .
H2C H 0.2426(17) 0.3793(16) 0.1389(9) 0.027(4) Uiso 1 1 d . . . . .
C3C C 0.23401(16) 0.25540(16) 0.04771(9) 0.0309(3) Uani 1 1 d . . . . .
H3CA H 0.161(2) 0.3464(18) 0.0212(10) 0.040(4) Uiso 1 1 d . . . . .
H3CB H 0.191(2) 0.1818(19) 0.0557(10) 0.043(4) Uiso 1 1 d . . . . .
C4C C 0.38412(16) 0.20095(14) -0.01099(8) 0.0297(3) Uani 1 1 d . . . . .
C5C C 0.23268(14) 0.19625(14) 0.21159(8) 0.0262(2) Uani 1 1 d . . . . .
C6C C 0.12115(16) 0.27488(16) 0.27336(9) 0.0358(3) Uani 1 1 d . . . . .
H6C H 0.0834(19) 0.3823(19) 0.2656(10) 0.041(4) Uiso 1 1 d . . . . .
C7C C 0.06967(18) 0.20200(19) 0.34539(10) 0.0444(4) Uani 1 1 d . . . . .
H7C H -0.009(2) 0.257(2) 0.3893(12) 0.056(5) Uiso 1 1 d . . . . .
C8C C 0.13035(18) 0.05123(19) 0.35736(10) 0.0426(4) Uani 1 1 d . . . . .
H8C H 0.093(2) -0.0001(19) 0.4100(12) 0.050(5) Uiso 1 1 d . . . . .
C9C C 0.24255(18) -0.02811(17) 0.29681(9) 0.0373(3) Uani 1 1 d . . . . .
H9C H 0.284(2) -0.136(2) 0.3059(11) 0.048(5) Uiso 1 1 d . . . . .
C10C C 0.29224(16) 0.04418(14) 0.22382(9) 0.0305(3) Uani 1 1 d . . . . .
H10C H 0.3703(19) -0.0118(17) 0.1804(10) 0.036(4) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1A 0.0327(6) 0.0624(7) 0.0412(6) -0.0134(5) 0.0046(5) -0.0018(5)
O2A 0.0322(5) 0.0377(5) 0.0294(5) -0.0087(4) 0.0008(4) -0.0105(4)
N1A 0.0256(5) 0.0266(5) 0.0299(6) -0.0032(4) -0.0024(4) -0.0077(4)
C1A 0.0327(7) 0.0269(6) 0.0303(7) -0.0038(5) 0.0005(5) -0.0081(5)
C2A 0.0340(7) 0.0259(6) 0.0284(6) -0.0041(5) -0.0008(5) -0.0146(5)
C3A 0.0249(6) 0.0340(7) 0.0298(6) -0.0046(5) -0.0008(5) -0.0130(5)
C4A 0.0275(6) 0.0214(5) 0.0290(6) -0.0025(5) -0.0001(5) -0.0120(5)
C5A 0.0286(6) 0.0293(6) 0.0281(6) -0.0038(5) 0.0018(5) -0.0111(5)
C6A 0.0341(7) 0.0294(7) 0.0327(7) -0.0059(5) -0.0029(5) -0.0083(6)
C7A 0.0375(8) 0.0440(8) 0.0326(7) -0.0101(6) -0.0042(6) -0.0038(6)
C8A 0.0404(8) 0.0510(9) 0.0317(8) 0.0055(7) 0.0015(6) -0.0071(7)
C9A 0.0535(10) 0.0437(9) 0.0467(9) 0.0079(7) 0.0030(7) -0.0246(8)
C10A 0.0500(9) 0.0400(8) 0.0390(8) 0.0000(6) -0.0019(7) -0.0264(7)
O1B 0.0473(6) 0.0292(5) 0.0527(6) -0.0033(4) -0.0021(5) -0.0205(5)
O2B 0.0289(5) 0.0412(5) 0.0395(5) -0.0022(4) 0.0051(4) -0.0188(4)
N1B 0.0252(5) 0.0249(5) 0.0304(6) -0.0056(4) 0.0023(4) -0.0071(4)
C1B 0.0257(6) 0.0271(6) 0.0309(6) -0.0008(5) -0.0042(5) -0.0109(5)
C2B 0.0209(6) 0.0271(6) 0.0309(6) -0.0033(5) 0.0000(5) -0.0103(5)
C3B 0.0312(7) 0.0293(7) 0.0356(7) -0.0081(5) 0.0058(5) -0.0161(6)
C4B 0.0205(5) 0.0281(6) 0.0297(6) -0.0008(5) -0.0030(5) -0.0086(5)
C5B 0.0256(6) 0.0310(6) 0.0317(6) -0.0046(5) 0.0001(5) -0.0142(5)
C6B 0.0276(6) 0.0300(7) 0.0366(7) -0.0039(5) 0.0018(5) -0.0100(5)
C7B 0.0375(8) 0.0397(8) 0.0405(8) -0.0106(6) 0.0091(6) -0.0160(6)
C8B 0.0544(10) 0.0551(10) 0.0299(7) -0.0076(7) 0.0020(7) -0.0291(8)
C9B 0.0434(9) 0.0691(12) 0.0395(9) 0.0028(8) -0.0136(7) -0.0216(8)
C10B 0.0265(7) 0.0599(10) 0.0397(8) -0.0027(7) -0.0043(6) -0.0141(7)
O1C 0.0325(5) 0.0409(5) 0.0384(5) 0.0007(4) -0.0088(4) -0.0206(4)
O2C 0.0490(6) 0.0593(7) 0.0336(6) -0.0102(5) -0.0020(5) -0.0255(6)
N1C 0.0238(5) 0.0289(5) 0.0313(6) -0.0010(4) -0.0006(4) -0.0110(4)
C1C 0.0263(6) 0.0213(5) 0.0322(6) 0.0019(5) -0.0033(5) -0.0124(5)
C2C 0.0248(6) 0.0215(6) 0.0317(6) -0.0014(5) -0.0022(5) -0.0076(5)
C3C 0.0261(6) 0.0343(7) 0.0323(7) 0.0034(5) -0.0060(5) -0.0135(6)
C4C 0.0323(7) 0.0268(6) 0.0311(7) 0.0017(5) -0.0042(5) -0.0142(5)
C5C 0.0213(6) 0.0287(6) 0.0274(6) -0.0019(5) -0.0028(5) -0.0091(5)
C6C 0.0297(7) 0.0332(7) 0.0339(7) -0.0054(6) -0.0011(5) -0.0020(6)
C7C 0.0329(7) 0.0551(10) 0.0311(7) -0.0056(7) 0.0055(6) -0.0059(7)
C8C 0.0373(8) 0.0549(9) 0.0312(7) 0.0064(7) 0.0004(6) -0.0192(7)
C9C 0.0388(8) 0.0346(7) 0.0378(8) 0.0031(6) -0.0032(6) -0.0166(6)
C10C 0.0289(6) 0.0295(6) 0.0321(7) -0.0038(5) 0.0017(5) -0.0120(5)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C1A 1.2065(17) . ?
O2A C4A 1.2280(16) . ?
N1A H1A 0.90(2) . ?
N1A C1A 1.3976(18) . ?
N1A C4A 1.3599(17) . ?
C1A C2A 1.522(2) . ?
C2A H2A 0.964(16) . ?
C2A C3A 1.5394(19) . ?
C2A C5A 1.5137(19) . ?
C3A H3AA 0.991(16) . ?
C3A H3AB 0.935(18) . ?
C3A C4A 1.4983(19) . ?
C5A C6A 1.3876(19) . ?
C5A C10A 1.395(2) . ?
C6A H6A 0.980(17) . ?
C6A C7A 1.391(2) . ?
C7A H7A 0.986(19) . ?
C7A C8A 1.378(3) . ?
C8A H8A 0.98(2) . ?
C8A C9A 1.381(3) . ?
C9A H9A 1.00(2) . ?
C9A C10A 1.392(2) . ?
C10A H10A 1.045(19) . ?
O1B C1B 1.2099(16) . ?
O2B C4B 1.2241(16) . ?
N1B H1B 0.878(16) . ?
N1B C1B 1.3852(17) . ?
N1B C4B 1.3677(18) . ?
C1B C2B 1.5232(19) . ?
C2B H2B 1.018(15) . ?
C2B C3B 1.5445(18) . ?
C2B C5B 1.5132(19) . ?
C3B H3BA 1.011(19) . ?
C3B H3BB 0.959(17) . ?
C3B C4B 1.5069(19) . ?
C5B C6B 1.3924(19) . ?
C5B C10B 1.388(2) . ?
C6B H6B 0.968(16) . ?
C6B C7B 1.389(2) . ?
C7B H7B 1.010(18) . ?
C7B C8B 1.377(2) . ?
C8B H8B 0.975(18) . ?
C8B C9B 1.387(3) . ?
C9B H9B 0.96(2) . ?
C9B C10B 1.390(2) . ?
C10B H10B 0.973(18) . ?
O1C C1C 1.2156(16) . ?
O2C C4C 1.2161(17) . ?
N1C H1C 0.910(19) . ?
N1C C1C 1.3754(18) . ?
N1C C4C 1.3828(18) . ?
C1C C2C 1.5307(19) . ?
C2C H2C 0.986(15) . ?
C2C C3C 1.542(2) . ?
C2C C5C 1.5170(18) . ?
C3C H3CA 0.962(17) . ?
C3C H3CB 0.964(18) . ?
C3C C4C 1.506(2) . ?
C5C C6C 1.3953(19) . ?
C5C C10C 1.3936(19) . ?
C6C H6C 0.986(17) . ?
C6C C7C 1.392(2) . ?
C7C H7C 0.984(19) . ?
C7C C8C 1.381(2) . ?
C8C H8C 1.006(18) . ?
C8C C9C 1.387(2) . ?
C9C H9C 0.986(18) . ?
C9C C10C 1.393(2) . ?
C10C H10C 0.983(16) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A N1A H1A 124.6(13) . . ?
C4A N1A H1A 121.6(13) . . ?
C4A N1A C1A 113.68(11) . . ?
O1A C1A N1A 123.62(13) . . ?
O1A C1A C2A 129.19(13) . . ?
N1A C1A C2A 107.14(11) . . ?
C1A C2A H2A 103.9(9) . . ?
C1A C2A C3A 103.56(11) . . ?
C3A C2A H2A 107.6(9) . . ?
C5A C2A C1A 114.93(11) . . ?
C5A C2A H2A 110.0(9) . . ?
C5A C2A C3A 115.95(11) . . ?
C2A C3A H3AA 110.8(9) . . ?
C2A C3A H3AB 114.1(11) . . ?
H3AA C3A H3AB 110.0(14) . . ?
C4A C3A C2A 104.85(11) . . ?
C4A C3A H3AA 106.5(9) . . ?
C4A C3A H3AB 110.2(11) . . ?
O2A C4A N1A 123.82(12) . . ?
O2A C4A C3A 127.52(12) . . ?
N1A C4A C3A 108.67(11) . . ?
C6A C5A C2A 119.71(12) . . ?
C6A C5A C10A 119.28(13) . . ?
C10A C5A C2A 120.97(12) . . ?
C5A C6A H6A 120.2(10) . . ?
C5A C6A C7A 120.38(14) . . ?
C7A C6A H6A 119.4(10) . . ?
C6A C7A H7A 119.2(11) . . ?
C8A C7A C6A 120.12(15) . . ?
C8A C7A H7A 120.6(11) . . ?
C7A C8A H8A 118.1(11) . . ?
C7A C8A C9A 119.99(15) . . ?
C9A C8A H8A 121.9(11) . . ?
C8A C9A H9A 123.0(12) . . ?
C8A C9A C10A 120.37(16) . . ?
C10A C9A H9A 116.7(12) . . ?
C5A C10A H10A 120.3(10) . . ?
C9A C10A C5A 119.85(15) . . ?
C9A C10A H10A 119.9(10) . . ?
C1B N1B H1B 123.3(10) . . ?
C4B N1B H1B 122.6(10) . . ?
C4B N1B C1B 114.02(11) . . ?
O1B C1B N1B 123.74(12) . . ?
O1B C1B C2B 128.68(12) . . ?
N1B C1B C2B 107.55(11) . . ?
C1B C2B H2B 102.9(8) . . ?
C1B C2B C3B 103.41(10) . . ?
C3B C2B H2B 108.5(8) . . ?
C5B C2B C1B 114.83(11) . . ?
C5B C2B H2B 109.9(8) . . ?
C5B C2B C3B 116.33(11) . . ?
C2B C3B H3BA 112.3(10) . . ?
C2B C3B H3BB 111.3(10) . . ?
H3BA C3B H3BB 111.1(14) . . ?
C4B C3B C2B 105.04(11) . . ?
C4B C3B H3BA 109.0(10) . . ?
C4B C3B H3BB 107.8(10) . . ?
O2B C4B N1B 124.36(12) . . ?
O2B C4B C3B 127.46(12) . . ?
N1B C4B C3B 108.17(11) . . ?
C6B C5B C2B 119.57(12) . . ?
C10B C5B C2B 121.68(12) . . ?
C10B C5B C6B 118.74(13) . . ?
C5B C6B H6B 118.5(9) . . ?
C7B C6B C5B 121.00(13) . . ?
C7B C6B H6B 120.5(9) . . ?
C6B C7B H7B 119.8(10) . . ?
C8B C7B C6B 119.96(14) . . ?
C8B C7B H7B 120.3(10) . . ?
C7B C8B H8B 119.9(11) . . ?
C7B C8B C9B 119.48(15) . . ?
C9B C8B H8B 120.5(11) . . ?
C8B C9B H9B 122.9(12) . . ?
C8B C9B C10B 120.75(15) . . ?
C10B C9B H9B 116.2(12) . . ?
C5B C10B C9B 120.06(15) . . ?
C5B C10B H10B 120.8(10) . . ?
C9B C10B H10B 119.1(10) . . ?
C1C N1C H1C 120.8(12) . . ?
C1C N1C C4C 113.93(11) . . ?
C4C N1C H1C 125.2(12) . . ?
O1C C1C N1C 124.34(12) . . ?
O1C C1C C2C 127.15(12) . . ?
N1C C1C C2C 108.50(10) . . ?
C1C C2C H2C 108.2(8) . . ?
C1C C2C C3C 103.62(10) . . ?
C3C C2C H2C 110.1(8) . . ?
C5C C2C C1C 112.18(10) . . ?
C5C C2C H2C 107.7(8) . . ?
C5C C2C C3C 114.86(11) . . ?
C2C C3C H3CA 111.8(10) . . ?
C2C C3C H3CB 112.6(10) . . ?
H3CA C3C H3CB 110.9(14) . . ?
C4C C3C C2C 105.72(11) . . ?
C4C C3C H3CA 108.8(10) . . ?
C4C C3C H3CB 106.7(10) . . ?
O2C C4C N1C 124.02(13) . . ?
O2C C4C C3C 127.89(13) . . ?
N1C C4C C3C 108.09(12) . . ?
C6C C5C C2C 120.66(12) . . ?
C10C C5C C2C 120.49(11) . . ?
C10C C5C C6C 118.83(12) . . ?
C5C C6C H6C 118.3(9) . . ?
C7C C6C C5C 120.28(14) . . ?
C7C C6C H6C 121.3(9) . . ?
C6C C7C H7C 120.8(11) . . ?
C8C C7C C6C 120.50(14) . . ?
C8C C7C H7C 118.7(11) . . ?
C7C C8C H8C 119.7(10) . . ?
C7C C8C C9C 119.72(14) . . ?
C9C C8C H8C 120.6(10) . . ?
C8C C9C H9C 118.7(10) . . ?
C8C C9C C10C 120.05(14) . . ?
C10C C9C H9C 121.2(10) . . ?
C5C C10C H10C 119.2(9) . . ?
C9C C10C C5C 120.60(13) . . ?
C9C C10C H10C 120.2(9) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1A O2A 0.90(2) 2.07(2) 2.9355(19) 162.1(18) 2_665 yes
N1B H1B O2A 0.878(16) 1.951(17) 2.8201(17) 170.1(15) . yes
N1C H1C O2B 0.910(19) 2.012(19) 2.9159(19) 171.7(18) . yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1A C1A C2A C3A 169.20(15) . . . . ?
O1A C1A C2A C5A 41.7(2) . . . . ?
N1A C1A C2A C3A -13.15(13) . . . . ?
N1A C1A C2A C5A -140.63(12) . . . . ?
C1A N1A C4A O2A -177.54(12) . . . . ?
C1A N1A C4A C3A 2.16(15) . . . . ?
C1A C2A C3A C4A 14.02(13) . . . . ?
C1A C2A C5A C6A -118.48(13) . . . . ?
C1A C2A C5A C10A 63.51(17) . . . . ?
C2A C3A C4A O2A 169.19(12) . . . . ?
C2A C3A C4A N1A -10.49(13) . . . . ?
C2A C5A C6A C7A -178.34(13) . . . . ?
C2A C5A C10A C9A 177.56(14) . . . . ?
C3A C2A C5A C6A 120.60(14) . . . . ?
C3A C2A C5A C10A -57.41(18) . . . . ?
C4A N1A C1A O1A -174.86(13) . . . . ?
C4A N1A C1A C2A 7.32(15) . . . . ?
C5A C2A C3A C4A 140.86(11) . . . . ?
C5A C6A C7A C8A 0.7(2) . . . . ?
C6A C5A C10A C9A -0.5(2) . . . . ?
C6A C7A C8A C9A -0.3(2) . . . . ?
C7A C8A C9A C10A -0.4(3) . . . . ?
C8A C9A C10A C5A 0.8(3) . . . . ?
C10A C5A C6A C7A -0.3(2) . . . . ?
O1B C1B C2B C3B -168.64(14) . . . . ?
O1B C1B C2B C5B -40.85(18) . . . . ?
N1B C1B C2B C3B 13.36(13) . . . . ?
N1B C1B C2B C5B 141.15(11) . . . . ?
C1B N1B C4B O2B -177.00(12) . . . . ?
C1B N1B C4B C3B 2.19(15) . . . . ?
C1B C2B C3B C4B -11.81(13) . . . . ?
C1B C2B C5B C6B 131.07(13) . . . . ?
C1B C2B C5B C10B -49.80(17) . . . . ?
C2B C3B C4B O2B -174.26(13) . . . . ?
C2B C3B C4B N1B 6.57(14) . . . . ?
C2B C5B C6B C7B 179.39(12) . . . . ?
C2B C5B C10B C9B -178.71(15) . . . . ?
C3B C2B C5B C6B -107.99(14) . . . . ?
C3B C2B C5B C10B 71.14(17) . . . . ?
C4B N1B C1B O1B 171.66(12) . . . . ?
C4B N1B C1B C2B -10.22(14) . . . . ?
C5B C2B C3B C4B -138.66(11) . . . . ?
C5B C6B C7B C8B -0.6(2) . . . . ?
C6B C5B C10B C9B 0.4(2) . . . . ?
C6B C7B C8B C9B 0.3(2) . . . . ?
C7B C8B C9B C10B 0.4(3) . . . . ?
C8B C9B C10B C5B -0.7(3) . . . . ?
C10B C5B C6B C7B 0.2(2) . . . . ?
O1C C1C C2C C3C -177.56(12) . . . . ?
O1C C1C C2C C5C -53.09(17) . . . . ?
N1C C1C C2C C3C 3.51(12) . . . . ?
N1C C1C C2C C5C 127.98(11) . . . . ?
C1C N1C C4C O2C 179.64(12) . . . . ?
C1C N1C C4C C3C -0.38(14) . . . . ?
C1C C2C C3C C4C -3.61(13) . . . . ?
C1C C2C C5C C6C 129.06(13) . . . . ?
C1C C2C C5C C10C -52.69(16) . . . . ?
C2C C3C C4C O2C -177.40(13) . . . . ?
C2C C3C C4C N1C 2.62(14) . . . . ?
C2C C5C C6C C7C 177.67(13) . . . . ?
C2C C5C C10C C9C -178.92(12) . . . . ?
C3C C2C C5C C6C -112.96(14) . . . . ?
C3C C2C C5C C10C 65.29(15) . . . . ?
C4C N1C C1C O1C 178.96(11) . . . . ?
C4C N1C C1C C2C -2.08(14) . . . . ?
C5C C2C C3C C4C -126.32(11) . . . . ?
C5C C6C C7C C8C 1.2(2) . . . . ?
C6C C5C C10C C9C -0.6(2) . . . . ?
C6C C7C C8C C9C -0.5(2) . . . . ?
C7C C8C C9C C10C -0.8(2) . . . . ?
C8C C9C C10C C5C 1.3(2) . . . . ?
C10C C5C C6C C7C -0.6(2) . . . . ?
_shelx_res_file
;
TITL Sena33_0m in P-1 #2
avk14f5.res
created by SHELXL-2018/1 at 15:39:22 on 27-Jul-2018
CELL 0.71073 9.2848 10.1182 15.9132 80.568 81.516 65.604
ZERR 6 0.0046 0.005 0.0079 0.006 0.006 0.006
LATT 1
SFAC C H N O
UNIT 60 54 6 12
EQIV $1 1-X,1-Y,-Z
L.S. 99
PLAN 20
SIZE 0.2 0.15 0.1
TEMP -173
HTAB N1A O2A_$1
HTAB N1B O2A
HTAB N1C O2B
BOND $H
CONF
fmap 2
acta
OMIT -1 1 0
OMIT 1 -1 2
OMIT 1 -1 1
OMIT -1 0 1
OMIT 1 0 0
OMIT 0 1 1
OMIT 1 0 1
OMIT 0 -1 1
REM
REM
REM
WGHT 0.060000 0.197700
FVAR 0.19229
O1A 4 0.340610 0.626228 0.238874 11.00000 0.03272 0.06236 =
0.04118 -0.01344 0.00459 -0.00179
O2A 4 0.699826 0.430049 0.018980 11.00000 0.03223 0.03775 =
0.02938 -0.00875 0.00076 -0.01049
N1A 3 0.496454 0.538494 0.117705 11.00000 0.02558 0.02663 =
0.02995 -0.00322 -0.00243 -0.00772
H1A 2 0.419092 0.560921 0.083172 11.00000 0.05822
C1A 1 0.470740 0.569439 0.202405 11.00000 0.03272 0.02691 =
0.03031 -0.00382 0.00051 -0.00812
C2A 1 0.633041 0.524085 0.234293 11.00000 0.03400 0.02590 =
0.02840 -0.00411 -0.00084 -0.01456
H2A 2 0.647029 0.614426 0.229023 11.00000 0.03417
C3A 1 0.748559 0.432127 0.165722 11.00000 0.02487 0.03403 =
0.02981 -0.00460 -0.00077 -0.01298
H3AA 2 0.782412 0.326401 0.185161 11.00000 0.03718
H3AB 2 0.837547 0.454247 0.148305 11.00000 0.04677
C4A 1 0.651823 0.463575 0.091796 11.00000 0.02753 0.02136 =
0.02900 -0.00254 -0.00009 -0.01199
C5A 1 0.648384 0.452361 0.325671 11.00000 0.02860 0.02928 =
0.02810 -0.00378 0.00181 -0.01107
C6A 1 0.682686 0.517170 0.386090 11.00000 0.03407 0.02936 =
0.03267 -0.00592 -0.00289 -0.00834
H6A 2 0.689687 0.612289 0.370686 11.00000 0.04098
C7A 1 0.701195 0.450642 0.469812 11.00000 0.03751 0.04397 =
0.03263 -0.01008 -0.00424 -0.00378
H7A 2 0.722366 0.499725 0.512265 11.00000 0.05445
C8A 1 0.687187 0.318844 0.493097 11.00000 0.04039 0.05098 =
0.03168 0.00545 0.00150 -0.00711
H8A 2 0.697264 0.276414 0.553154 11.00000 0.05594
C9A 1 0.653953 0.252954 0.433368 11.00000 0.05350 0.04366 =
0.04667 0.00793 0.00304 -0.02459
H9A 2 0.642896 0.157279 0.447128 11.00000 0.06733
C10A 1 0.633365 0.319380 0.349680 11.00000 0.05005 0.03996 =
0.03899 -0.00002 -0.00186 -0.02638
H10A 2 0.607566 0.269039 0.304964 11.00000 0.05586
O1B 4 1.046578 0.378781 -0.159093 11.00000 0.04735 0.02917 =
0.05273 -0.00331 -0.00210 -0.02051
O2B 4 0.834466 0.050027 -0.043816 11.00000 0.02890 0.04120 =
0.03955 -0.00215 0.00511 -0.01880
N1B 3 0.930334 0.228627 -0.085443 11.00000 0.02518 0.02491 =
0.03041 -0.00555 0.00232 -0.00714
H1B 2 0.867571 0.288936 -0.048959 11.00000 0.03479
C1B 1 1.037210 0.261257 -0.146501 11.00000 0.02571 0.02710 =
0.03087 -0.00078 -0.00419 -0.01091
C2B 1 1.137727 0.123746 -0.189263 11.00000 0.02090 0.02715 =
0.03087 -0.00335 0.00003 -0.01026
H2B 2 1.239233 0.081844 -0.159023 11.00000 0.03060
C3B 1 1.046397 0.024233 -0.159884 11.00000 0.03120 0.02925 =
0.03556 -0.00810 0.00584 -0.01611
H3BA 2 1.117681 -0.077427 -0.136243 11.00000 0.05056
H3BB 2 0.990219 0.020935 -0.204971 11.00000 0.04004
C4B 1 0.925119 0.096759 -0.089646 11.00000 0.02052 0.02808 =
0.02969 -0.00082 -0.00299 -0.00863
C5B 1 1.176410 0.149844 -0.284670 11.00000 0.02562 0.03103 =
0.03167 -0.00463 0.00007 -0.01420
C6B 1 1.332511 0.084827 -0.319728 11.00000 0.02757 0.02996 =
0.03660 -0.00388 0.00183 -0.01003
H6B 2 1.413535 0.024460 -0.281807 11.00000 0.03423
C7B 1 1.371762 0.105458 -0.407166 11.00000 0.03748 0.03968 =
0.04047 -0.01064 0.00909 -0.01603
H7B 2 1.485898 0.058332 -0.431244 11.00000 0.04848
C8B 1 1.255164 0.190224 -0.460616 11.00000 0.05445 0.05505 =
0.02990 -0.00757 0.00201 -0.02915
H8B 2 1.283445 0.208738 -0.521551 11.00000 0.05102
C9B 1 1.099134 0.254960 -0.426363 11.00000 0.04341 0.06907 =
0.03953 0.00283 -0.01364 -0.02161
H9B 2 1.014680 0.320664 -0.460019 11.00000 0.06746
C10B 1 1.059591 0.235827 -0.338845 11.00000 0.02647 0.05987 =
0.03970 -0.00270 -0.00425 -0.01407
H10B 2 0.950281 0.286517 -0.316134 11.00000 0.04651
O1C 4 0.558062 0.209351 0.165330 11.00000 0.03252 0.04090 =
0.03839 0.00066 -0.00879 -0.02055
O2C 4 0.398100 0.175671 -0.084567 11.00000 0.04905 0.05926 =
0.03359 -0.01016 -0.00203 -0.02547
N1C 3 0.509708 0.183032 0.033180 11.00000 0.02382 0.02892 =
0.03131 -0.00105 -0.00057 -0.01103
H1C 2 0.613871 0.145825 0.012852 11.00000 0.05489
C1C 1 0.465766 0.219147 0.115493 11.00000 0.02630 0.02128 =
0.03220 0.00193 -0.00332 -0.01239
C2C 1 0.284830 0.274774 0.131290 11.00000 0.02478 0.02153 =
0.03169 -0.00135 -0.00222 -0.00760
H2C 2 0.242555 0.379253 0.138905 11.00000 0.02725
C3C 1 0.234014 0.255397 0.047712 11.00000 0.02615 0.03435 =
0.03226 0.00337 -0.00603 -0.01352
H3CA 2 0.161198 0.346428 0.021156 11.00000 0.03996
H3CB 2 0.191063 0.181828 0.055676 11.00000 0.04295
C4C 1 0.384116 0.200949 -0.010993 11.00000 0.03226 0.02678 =
0.03109 0.00166 -0.00422 -0.01418
C5C 1 0.232677 0.196252 0.211592 11.00000 0.02134 0.02874 =
0.02745 -0.00193 -0.00280 -0.00908
C6C 1 0.121152 0.274885 0.273359 11.00000 0.02975 0.03325 =
0.03386 -0.00535 -0.00105 -0.00202
H6C 2 0.083369 0.382289 0.265614 11.00000 0.04079
C7C 1 0.069674 0.202002 0.345390 11.00000 0.03288 0.05509 =
0.03109 -0.00556 0.00550 -0.00594
H7C 2 -0.008898 0.256635 0.389251 11.00000 0.05617
C8C 1 0.130349 0.051226 0.357356 11.00000 0.03729 0.05486 =
0.03119 0.00638 0.00045 -0.01924
H8C 2 0.093071 -0.000054 0.409999 11.00000 0.04974
C9C 1 0.242546 -0.028114 0.296812 11.00000 0.03876 0.03460 =
0.03780 0.00307 -0.00315 -0.01662
H9C 2 0.283549 -0.135643 0.305940 11.00000 0.04833
C10C 1 0.292238 0.044175 0.223825 11.00000 0.02887 0.02951 =
0.03206 -0.00379 0.00167 -0.01205
H10C 2 0.370312 -0.011778 0.180372 11.00000 0.03572
HKLF 4
REM Sena33_0m in P-1 #2
REM R1 = 0.0470 for 5607 Fo > 4sig(Fo) and 0.0762 for all 8123 data
REM 460 parameters refined using 0 restraints
END
WGHT 0.0600 0.1972
REM Highest difference peak 0.381, deepest hole -0.241, 1-sigma level 0.047
Q1 1 1.1572 0.1352 -0.2384 11.00000 0.05 0.38
Q2 1 0.9940 0.0427 -0.1208 11.00000 0.05 0.28
Q3 1 0.6296 0.5048 0.2858 11.00000 0.05 0.26
Q4 1 1.3478 0.1027 -0.3643 11.00000 0.05 0.24
Q5 1 1.0797 0.1928 -0.1719 11.00000 0.05 0.23
Q6 1 1.2585 0.1127 -0.3024 11.00000 0.05 0.23
Q7 1 0.6843 0.4720 0.2022 11.00000 0.05 0.23
Q8 1 0.5717 0.4960 0.1051 11.00000 0.05 0.23
Q9 1 0.5784 0.2157 0.1100 11.00000 0.05 0.22
Q10 1 0.7930 0.0444 0.0055 11.00000 0.05 0.22
Q11 1 0.5211 0.2171 0.2261 11.00000 0.05 0.21
Q12 1 0.2403 0.2519 0.0978 11.00000 0.05 0.21
Q13 1 1.3068 0.1595 -0.4217 11.00000 0.05 0.21
Q14 1 0.4840 0.5460 0.1599 11.00000 0.05 0.21
Q15 1 0.2498 0.2474 0.1688 11.00000 0.05 0.20
Q16 1 0.4975 0.1746 0.0793 11.00000 0.05 0.20
Q17 1 0.2471 0.1269 0.2178 11.00000 0.05 0.20
Q18 1 0.5150 0.2583 0.0557 11.00000 0.05 0.19
Q19 1 0.7089 0.4425 0.1266 11.00000 0.05 0.19
Q20 1 0.7217 0.4251 -0.0444 11.00000 0.05 0.19
;
_shelx_res_checksum 70557
_olex2_submission_original_sample_id AVK14F5
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_PII_100K
_database_code_depnum_ccdc_archive 'CCDC 1957488'
loop_
_audit_author_name
_audit_author_address
'Tatiana Timofeeva'
;New Mexico Highlands University
United States of America
;
_audit_update_record
;
2019-10-03 deposited with the CCDC. 2019-10-14 downloaded from the CCDC.
;
_audit_creation_date 2019-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common ?
_chemical_name_systematic rac-3-phenylpyrrolidin-2,5-dione
_chemical_formula_moiety 'C10 H9 N O2'
_chemical_formula_sum 'C10 H9 N O2'
_chemical_formula_weight 175.18
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 15.51(14)
_cell_length_b 5.64(5)
_cell_length_c 20.49(16)
_cell_angle_alpha 90
_cell_angle_beta 108.10(10)
_cell_angle_gamma 90
_cell_volume 1704(25)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 383
_cell_measurement_temperature 100.0
_cell_measurement_theta_max 17.581
_cell_measurement_theta_min 3.756
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.096
_exptl_absorpt_correction_T_max 0.7442
_exptl_absorpt_correction_T_min 0.3098
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1340 before and 0.0496 after correction. The Ratio of minimum to maximum transmission is 0.4163. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.366
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plate
_exptl_crystal_F_000 736
_exptl_crystal_size_max 0.3
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.1
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.1999
_diffrn_reflns_av_unetI/netI 0.1558
_diffrn_reflns_Laue_measured_fraction_full 0.934
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 4
_diffrn_reflns_limit_k_min -4
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 2613
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full 17.869
_diffrn_reflns_theta_max 17.869
_diffrn_reflns_theta_min 2.091
_diffrn_ambient_temperature 100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 473
_reflns_number_total 1071
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT V8.38A (?, 2016)'
_computing_data_collection ?
_computing_data_reduction 'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max 0.209
_refine_diff_density_min -0.210
_refine_diff_density_rms 0.055
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.866
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 235
_refine_ls_number_reflns 1071
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1352
_refine_ls_R_factor_gt 0.0691
_refine_ls_restrained_S_all 0.866
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0696P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1326
_refine_ls_wR_factor_ref 0.1687
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
C3(H3), C3A(H3A)
2.b Secondary CH2 refined with riding coordinates:
C2(H2A,H2B), C2A(H2AA,H2AB)
2.c Aromatic/amide H refined with riding coordinates:
N1(H1), N1A(H1A), C6(H6), C10A(H10A), C7(H7), C9A(H9A), C8(H8), C8A(H8A),
C9(H9), C7A(H7A), C10(H10), C6A(H6A)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.3392(7) 0.1477(17) 0.6173(4) 0.072(3) Uani 1 1 d . . . . .
O2A O 0.6087(5) 0.3625(14) 0.6567(4) 0.060(3) Uani 1 1 d . . . . .
O1 O 0.5731(7) -0.1739(17) 0.5589(4) 0.069(3) Uani 1 1 d . . . . .
O1A O 0.5860(7) 1.0246(14) 0.7715(3) 0.059(3) Uani 1 1 d . . . . .
N1 N 0.4677(10) 0.0173(18) 0.5987(4) 0.051(3) Uani 1 1 d . . . . .
H1 H 0.502560 0.132201 0.621472 0.061 Uiso 1 1 calc R . . . .
N1A N 0.5833(7) 0.668(2) 0.7189(5) 0.042(3) Uani 1 1 d . . . . .
H1A H 0.529784 0.622052 0.720752 0.051 Uiso 1 1 calc R . . . .
C4 C 0.3818(13) 0.000(3) 0.5972(6) 0.059(5) Uani 1 1 d . . . . .
C4A C 0.6345(11) 0.540(3) 0.6887(7) 0.053(4) Uani 1 1 d . . . . .
C1 C 0.5011(11) -0.152(3) 0.5630(7) 0.052(4) Uani 1 1 d . . . . .
C1A C 0.6247(10) 0.877(3) 0.7464(6) 0.047(4) Uani 1 1 d . . . . .
C2 C 0.4167(10) -0.3130(19) 0.5321(6) 0.060(4) Uani 1 1 d . . . . .
H2A H 0.393125 -0.293581 0.481584 0.072 Uiso 1 1 calc R . . . .
H2B H 0.432617 -0.481584 0.542649 0.072 Uiso 1 1 calc R . . . .
C2A C 0.7122(11) 0.8916(18) 0.7350(6) 0.066(4) Uani 1 1 d . . . . .
H2AA H 0.761060 0.908038 0.779312 0.079 Uiso 1 1 calc R . . . .
H2AB H 0.714082 1.030819 0.706083 0.079 Uiso 1 1 calc R . . . .
C3 C 0.3477(10) -0.234(2) 0.5648(6) 0.054(4) Uani 1 1 d . . . . .
H3 H 0.352770 -0.346325 0.603574 0.065 Uiso 1 1 calc R . . . .
C3A C 0.7248(9) 0.664(2) 0.6990(5) 0.045(3) Uani 1 1 d . . . . .
H3A H 0.730800 0.704479 0.653056 0.053 Uiso 1 1 calc R . . . .
C5 C 0.2489(9) -0.237(3) 0.5214(6) 0.046(4) Uani 1 1 d . . . . .
C5A C 0.8020(9) 0.510(2) 0.7367(9) 0.044(4) Uani 1 1 d . . . . .
C6 C 0.1942(14) -0.419(2) 0.5208(6) 0.059(4) Uani 1 1 d . . . . .
H6 H 0.217066 -0.552438 0.549256 0.071 Uiso 1 1 calc R . . . .
C10A C 0.8497(13) 0.383(3) 0.7060(6) 0.062(4) Uani 1 1 d . . . . .
H10A H 0.834697 0.396075 0.657542 0.075 Uiso 1 1 calc R . . . .
C7 C 0.1045(14) -0.418(3) 0.4796(8) 0.083(5) Uani 1 1 d . . . . .
H7 H 0.066315 -0.549522 0.479616 0.100 Uiso 1 1 calc R . . . .
C9A C 0.9194(10) 0.231(2) 0.7390(10) 0.066(4) Uani 1 1 d . . . . .
H9A H 0.953236 0.149753 0.714442 0.079 Uiso 1 1 calc R . . . .
C8 C 0.0722(9) -0.230(4) 0.4396(7) 0.068(4) Uani 1 1 d . . . . .
H8 H 0.010071 -0.223743 0.412717 0.081 Uiso 1 1 calc R . . . .
C8A C 0.9378(10) 0.204(2) 0.8070(10) 0.062(4) Uani 1 1 d . . . . .
H8A H 0.985738 0.102527 0.831945 0.075 Uiso 1 1 calc R . . . .
C9 C 0.1295(17) -0.049(2) 0.4381(7) 0.088(6) Uani 1 1 d . . . . .
H9 H 0.107635 0.081936 0.408232 0.106 Uiso 1 1 calc R . . . .
C7A C 0.8872(13) 0.322(3) 0.8393(6) 0.063(4) Uani 1 1 d . . . . .
H7A H 0.900153 0.298618 0.887352 0.075 Uiso 1 1 calc R . . . .
C10 C 0.2177(12) -0.052(3) 0.4787(8) 0.084(5) Uani 1 1 d . . . . .
H10 H 0.257104 0.075694 0.476967 0.101 Uiso 1 1 calc R . . . .
C6A C 0.8177(10) 0.474(2) 0.8066(9) 0.059(4) Uani 1 1 d . . . . .
H6A H 0.782079 0.550118 0.830605 0.071 Uiso 1 1 calc R . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.075(9) 0.070(7) 0.061(7) -0.023(5) 0.006(5) 0.007(6)
O2A 0.081(7) 0.030(5) 0.052(6) 0.005(4) -0.004(4) -0.005(5)
O1 0.079(9) 0.063(6) 0.055(6) -0.004(4) 0.003(6) 0.012(7)
O1A 0.077(8) 0.052(6) 0.044(5) -0.006(4) 0.013(5) 0.015(5)
N1 0.077(12) 0.042(7) 0.023(6) -0.010(5) -0.001(6) -0.001(8)
N1A 0.035(8) 0.043(7) 0.041(6) 0.005(6) -0.001(6) -0.013(8)
C4 0.071(17) 0.056(15) 0.035(9) 0.017(9) -0.006(9) -0.009(11)
C4A 0.073(15) 0.035(10) 0.039(9) 0.009(8) 0.000(9) 0.015(11)
C1 0.058(14) 0.049(10) 0.036(9) 0.014(8) -0.002(10) 0.018(12)
C1A 0.038(12) 0.057(13) 0.036(9) 0.025(9) -0.002(8) 0.003(10)
C2 0.084(12) 0.029(8) 0.050(8) -0.012(7) 0.000(8) 0.011(8)
C2A 0.082(15) 0.023(9) 0.080(10) -0.008(7) 0.007(8) 0.007(8)
C3 0.095(15) 0.028(9) 0.033(8) -0.002(6) 0.010(9) -0.001(8)
C3A 0.044(11) 0.038(8) 0.050(8) -0.003(7) 0.011(7) 0.007(9)
C5 0.052(12) 0.045(10) 0.029(9) -0.014(8) -0.008(8) 0.015(10)
C5A 0.046(11) 0.026(8) 0.045(13) -0.021(8) -0.008(8) -0.004(8)
C6 0.097(15) 0.040(11) 0.045(11) -0.030(7) 0.028(11) -0.014(10)
C10A 0.097(14) 0.025(8) 0.046(10) -0.014(9) -0.006(11) -0.009(8)
C7 0.090(17) 0.078(16) 0.068(11) -0.035(11) 0.005(10) -0.041(11)
C9A 0.085(14) 0.048(10) 0.058(13) -0.006(8) 0.014(8) 0.019(8)
C8 0.049(12) 0.065(12) 0.078(12) -0.024(10) 0.003(8) 0.021(11)
C8A 0.062(12) 0.043(9) 0.071(15) 0.009(9) 0.004(10) 0.000(8)
C9 0.16(2) 0.029(10) 0.054(11) -0.010(8) 0.004(13) 0.014(12)
C7A 0.082(13) 0.064(10) 0.030(9) 0.004(10) 0.000(11) -0.004(9)
C10 0.085(15) 0.077(14) 0.048(10) -0.013(10) -0.042(9) -0.012(9)
C6A 0.072(13) 0.050(10) 0.045(13) -0.006(8) 0.002(8) 0.009(9)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C4 1.214(17) . ?
O2A C4A 1.197(15) . ?
O1 C1 1.153(18) . ?
O1A C1A 1.229(16) . ?
N1 H1 0.8800 . ?
N1 C4 1.33(2) . ?
N1 C1 1.395(18) . ?
N1A H1A 0.8800 . ?
N1A C4A 1.355(16) . ?
N1A C1A 1.379(17) . ?
C4 C3 1.50(2) . ?
C4A C3A 1.52(2) . ?
C1 C2 1.56(2) . ?
C1A C2A 1.45(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.497(19) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C2A C3A 1.524(16) . ?
C3 H3 1.0000 . ?
C3 C5 1.514(19) . ?
C3A H3A 1.0000 . ?
C3A C5A 1.486(17) . ?
C5 C6 1.333(16) . ?
C5 C10 1.352(16) . ?
C5A C10A 1.323(17) . ?
C5A C6A 1.391(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.38(2) . ?
C10A H10A 0.9500 . ?
C10A C9A 1.379(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.337(16) . ?
C9A H9A 0.9500 . ?
C9A C8A 1.342(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.365(19) . ?
C8A H8A 0.9500 . ?
C8A C7A 1.351(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.36(2) . ?
C7A H7A 0.9500 . ?
C7A C6A 1.378(16) . ?
C10 H10 0.9500 . ?
C6A H6A 0.9500 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 H1 121.0 . . ?
C4 N1 C1 118.0(14) . . ?
C1 N1 H1 121.0 . . ?
C4A N1A H1A 124.0 . . ?
C4A N1A C1A 112.1(14) . . ?
C1A N1A H1A 124.0 . . ?
O2 C4 N1 126.1(16) . . ?
O2 C4 C3 127.1(18) . . ?
N1 C4 C3 106.8(14) . . ?
O2A C4A N1A 123.5(16) . . ?
O2A C4A C3A 126.7(15) . . ?
N1A C4A C3A 109.8(13) . . ?
O1 C1 N1 129.6(16) . . ?
O1 C1 C2 128.1(15) . . ?
N1 C1 C2 102.2(14) . . ?
O1A C1A N1A 121.7(16) . . ?
O1A C1A C2A 129.2(15) . . ?
N1A C1A C2A 108.9(13) . . ?
C1 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
C3 C2 C1 105.7(12) . . ?
C3 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
C1A C2A H2AA 110.3 . . ?
C1A C2A H2AB 110.3 . . ?
C1A C2A C3A 107.3(11) . . ?
H2AA C2A H2AB 108.5 . . ?
C3A C2A H2AA 110.3 . . ?
C3A C2A H2AB 110.3 . . ?
C4 C3 C2 105.0(13) . . ?
C4 C3 H3 106.0 . . ?
C4 C3 C5 115.0(13) . . ?
C2 C3 H3 106.0 . . ?
C2 C3 C5 117.8(13) . . ?
C5 C3 H3 106.0 . . ?
C4A C3A C2A 101.7(11) . . ?
C4A C3A H3A 109.1 . . ?
C2A C3A H3A 109.1 . . ?
C5A C3A C4A 111.2(12) . . ?
C5A C3A C2A 116.3(11) . . ?
C5A C3A H3A 109.1 . . ?
C6 C5 C3 122.5(16) . . ?
C6 C5 C10 119.5(13) . . ?
C10 C5 C3 117.8(16) . . ?
C10A C5A C3A 123.3(17) . . ?
C10A C5A C6A 117.6(12) . . ?
C6A C5A C3A 118.5(16) . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.2(12) . . ?
C7 C6 H6 119.4 . . ?
C5A C10A H10A 117.5 . . ?
C5A C10A C9A 125.0(13) . . ?
C9A C10A H10A 117.5 . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.5(13) . . ?
C8 C7 H7 120.2 . . ?
C10A C9A H9A 121.2 . . ?
C8A C9A C10A 117.5(12) . . ?
C8A C9A H9A 121.2 . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.1(14) . . ?
C9 C8 H8 120.5 . . ?
C9A C8A H8A 120.5 . . ?
C9A C8A C7A 118.9(13) . . ?
C7A C8A H8A 120.5 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(13) . . ?
C10 C9 H9 119.5 . . ?
C8A C7A H7A 118.2 . . ?
C8A C7A C6A 123.6(13) . . ?
C6A C7A H7A 118.2 . . ?
C5 C10 C9 119.6(14) . . ?
C5 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C5A C6A H6A 121.5 . . ?
C7A C6A C5A 117.0(12) . . ?
C7A C6A H6A 121.5 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1A O1A 0.88 1.93 2.81(3) 177.8 2_646 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C4 C3 C2 164.1(12) . . . . ?
O2 C4 C3 C5 33.0(19) . . . . ?
O2A C4A C3A C2A 172.7(10) . . . . ?
O2A C4A C3A C5A -62.8(15) . . . . ?
O1 C1 C2 C3 168.4(13) . . . . ?
O1A C1A C2A C3A -177.0(10) . . . . ?
N1 C4 C3 C2 -14.6(12) . . . . ?
N1 C4 C3 C5 -145.7(12) . . . . ?
N1 C1 C2 C3 -9.2(11) . . . . ?
N1A C4A C3A C2A -4.3(11) . . . . ?
N1A C4A C3A C5A 120.2(12) . . . . ?
N1A C1A C2A C3A -1.9(11) . . . . ?
C4 N1 C1 O1 -177.6(13) . . . . ?
C4 N1 C1 C2 -0.1(12) . . . . ?
C4 C3 C5 C6 -141.0(12) . . . . ?
C4 C3 C5 C10 43.2(17) . . . . ?
C4A N1A C1A O1A 174.6(10) . . . . ?
C4A N1A C1A C2A -1.0(11) . . . . ?
C4A C3A C5A C10A 98.2(15) . . . . ?
C4A C3A C5A C6A -72.9(14) . . . . ?
C1 N1 C4 O2 -169.3(11) . . . . ?
C1 N1 C4 C3 9.4(13) . . . . ?
C1 C2 C3 C4 14.3(11) . . . . ?
C1 C2 C3 C5 143.8(12) . . . . ?
C1A N1A C4A O2A -173.6(9) . . . . ?
C1A N1A C4A C3A 3.5(11) . . . . ?
C1A C2A C3A C4A 3.6(11) . . . . ?
C1A C2A C3A C5A -117.4(13) . . . . ?
C2 C3 C5 C6 94.4(16) . . . . ?
C2 C3 C5 C10 -81.4(15) . . . . ?
C2A C3A C5A C10A -146.0(13) . . . . ?
C2A C3A C5A C6A 42.9(17) . . . . ?
C3 C5 C6 C7 -178.8(12) . . . . ?
C3 C5 C10 C9 179.2(13) . . . . ?
C3A C5A C10A C9A -177.4(11) . . . . ?
C3A C5A C6A C7A 177.0(11) . . . . ?
C5 C6 C7 C8 0(2) . . . . ?
C5A C10A C9A C8A 3(2) . . . . ?
C6 C5 C10 C9 3(2) . . . . ?
C6 C7 C8 C9 3(2) . . . . ?
C10A C5A C6A C7A 5.4(17) . . . . ?
C10A C9A C8A C7A 0.7(18) . . . . ?
C7 C8 C9 C10 -3(2) . . . . ?
C9A C8A C7A C6A -1(2) . . . . ?
C8 C9 C10 C5 0(2) . . . . ?
C8A C7A C6A C5A -2.1(19) . . . . ?
C10 C5 C6 C7 -3.1(19) . . . . ?
C6A C5A C10A C9A -6(2) . . . . ?
_shelx_res_file
;
TITL poly2_a.res in P2(1)/c
poly2.res
created by SHELXL-2017/1 at 12:15:55 on 24-Sep-2019
REM Old TITL poly2 in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.223, Rweak 0.006, Alpha 0.051, Orientation as input
REM Formula found by SHELXT: C20 N3 O3
CELL 0.71073 15.5052 5.6431 20.4898 90 108.098 90
ZERR 8 0.1392 0.0454 0.1625 0 0.101 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 80 72 8 16
EQIV $1 1-X,-0.5+Y,1.5-Z
L.S. 4 0 0
PLAN 20
TEMP -123
HTAB N1A O1A_$1
BOND $H
BOND
list 4
conf
fmap 2 53
acta
OMIT -8 2 13
OMIT -8 1 4
OMIT -9 1 8
OMIT -6 2 9
OMIT -7 1 5
OMIT 6 1 0
OMIT -7 1 7
OMIT 3 0 0
OMIT -1 1 1
OMIT -7 2 10
OMIT -1 0 4
OMIT -6 1 2
OMIT -10 1 7
OMIT -2 0 6
REM
REM
REM
WGHT 0.069600
FVAR 0.54560
O2 4 0.339159 0.147729 0.617274 11.00000 0.07457 0.07009 =
0.06059 -0.02332 0.00649 0.00731
O2A 4 0.608717 0.362546 0.656665 11.00000 0.08120 0.03030 =
0.05232 0.00485 -0.00402 -0.00458
O1 4 0.573114 -0.173892 0.558918 11.00000 0.07890 0.06261 =
0.05478 -0.00376 0.00311 0.01244
O1A 4 0.586039 1.024631 0.771497 11.00000 0.07696 0.05222 =
0.04414 -0.00611 0.01313 0.01451
N1 3 0.467668 0.017279 0.598678 11.00000 0.07672 0.04161 =
0.02319 -0.00999 -0.00145 -0.00126
AFIX 43
H1 2 0.502560 0.132201 0.621472 11.00000 -1.20000
AFIX 0
N1A 3 0.583265 0.667579 0.718919 11.00000 0.03493 0.04301 =
0.04077 0.00458 -0.00061 -0.01338
AFIX 43
H1A 2 0.529784 0.622052 0.720752 11.00000 -1.20000
AFIX 0
C4 1 0.381765 -0.000394 0.597220 11.00000 0.07133 0.05590 =
0.03494 0.01659 -0.00620 -0.00870
C4A 1 0.634527 0.540133 0.688729 11.00000 0.07346 0.03527 =
0.03884 0.00889 -0.00003 0.01453
C1 1 0.501053 -0.151686 0.563015 11.00000 0.05812 0.04900 =
0.03590 0.01377 -0.00210 0.01767
C1A 1 0.624717 0.876879 0.746418 11.00000 0.03772 0.05740 =
0.03565 0.02491 -0.00178 0.00253
C2 1 0.416714 -0.312964 0.532052 11.00000 0.08424 0.02941 =
0.05048 -0.01165 -0.00037 0.01064
AFIX 23
H2A 2 0.393125 -0.293581 0.481584 11.00000 -1.20000
H2B 2 0.432617 -0.481584 0.542649 11.00000 -1.20000
AFIX 0
C2A 1 0.712151 0.891625 0.735006 11.00000 0.08168 0.02260 =
0.08041 -0.00825 0.00657 0.00702
AFIX 23
H2AA 2 0.761060 0.908038 0.779312 11.00000 -1.20000
H2AB 2 0.714082 1.030819 0.706083 11.00000 -1.20000
AFIX 0
C3 1 0.347693 -0.233957 0.564820 11.00000 0.09499 0.02838 =
0.03280 -0.00160 0.00992 -0.00108
AFIX 13
H3 2 0.352770 -0.346325 0.603574 11.00000 -1.20000
AFIX 0
C3A 1 0.724760 0.663988 0.698950 11.00000 0.04384 0.03775 =
0.04959 -0.00344 0.01105 0.00731
AFIX 13
H3A 2 0.730800 0.704479 0.653056 11.00000 -1.20000
AFIX 0
C5 1 0.248915 -0.236578 0.521382 11.00000 0.05160 0.04450 =
0.02941 -0.01368 -0.00764 0.01479
C5A 1 0.802025 0.510384 0.736695 11.00000 0.04642 0.02583 =
0.04454 -0.02100 -0.00793 -0.00392
C6 1 0.194175 -0.419151 0.520831 11.00000 0.09741 0.03973 =
0.04523 -0.02978 0.02829 -0.01350
AFIX 43
H6 2 0.217066 -0.552438 0.549256 11.00000 -1.20000
AFIX 0
C10A 1 0.849688 0.382582 0.706006 11.00000 0.09674 0.02455 =
0.04617 -0.01415 -0.00625 -0.00874
AFIX 43
H10A 2 0.834697 0.396075 0.657542 11.00000 -1.20000
AFIX 0
C7 1 0.104531 -0.417986 0.479559 11.00000 0.09024 0.07773 =
0.06790 -0.03494 0.00540 -0.04126
AFIX 43
H7 2 0.066315 -0.549522 0.479616 11.00000 -1.20000
AFIX 0
C9A 1 0.919446 0.231323 0.738969 11.00000 0.08456 0.04838 =
0.05824 -0.00551 0.01443 0.01939
AFIX 43
H9A 2 0.953236 0.149753 0.714442 11.00000 -1.20000
AFIX 0
C8 1 0.072159 -0.230414 0.439634 11.00000 0.04863 0.06453 =
0.07819 -0.02374 0.00340 0.02109
AFIX 43
H8 2 0.010071 -0.223743 0.412717 11.00000 -1.20000
AFIX 0
C8A 1 0.937846 0.203583 0.806962 11.00000 0.06169 0.04335 =
0.07114 0.00938 0.00419 -0.00019
AFIX 43
H8A 2 0.985738 0.102527 0.831945 11.00000 -1.20000
AFIX 0
C9 1 0.129531 -0.048582 0.438068 11.00000 0.16195 0.02851 =
0.05412 -0.01006 0.00354 0.01355
AFIX 43
H9 2 0.107635 0.081936 0.408232 11.00000 -1.20000
AFIX 0
C7A 1 0.887163 0.321693 0.839332 11.00000 0.08211 0.06419 =
0.02971 0.00434 -0.00032 -0.00411
AFIX 43
H7A 2 0.900153 0.298618 0.887352 11.00000 -1.20000
AFIX 0
C10 1 0.217737 -0.051539 0.478666 11.00000 0.08469 0.07738 =
0.04780 -0.01268 -0.04169 -0.01212
AFIX 43
H10 2 0.257104 0.075694 0.476967 11.00000 -1.20000
AFIX 0
C6A 1 0.817695 0.473722 0.806562 11.00000 0.07153 0.04984 =
0.04488 -0.00589 0.00226 0.00913
AFIX 43
H6A 2 0.782079 0.550118 0.830605 11.00000 -1.20000
AFIX 0
HKLF 4
REM poly2_a.res in P2(1)/c
REM R1 = 0.0691 for 473 Fo > 4sig(Fo) and 0.1352 for all 1071 data
REM 235 parameters refined using 0 restraints
END
WGHT 0.0696 0.0000
REM Highest difference peak 0.209, deepest hole -0.210, 1-sigma level 0.055
Q1 1 0.2617 -0.6477 0.5201 11.00000 0.05 0.21
Q2 1 0.6455 1.0165 0.7217 11.00000 0.05 0.19
Q3 1 0.7360 0.6220 0.8216 11.00000 0.05 0.18
Q4 1 0.5893 0.4269 0.7965 11.00000 0.05 0.18
Q5 1 0.5068 0.8884 0.7595 11.00000 0.05 0.18
Q6 1 0.6393 1.2648 0.7632 11.00000 0.05 0.17
Q7 1 0.4522 -0.4870 0.5032 11.00000 0.05 0.17
Q8 1 0.3275 -0.4933 0.4960 11.00000 0.05 0.17
Q9 1 0.8310 0.8504 0.7263 11.00000 0.05 0.16
Q10 1 0.8638 0.6991 0.7450 11.00000 0.05 0.16
Q11 1 0.3441 -0.5516 0.4765 11.00000 0.05 0.16
Q12 1 0.3932 -0.0387 0.4811 11.00000 0.05 0.16
Q13 1 0.3662 -0.6509 0.5348 11.00000 0.05 0.15
Q14 1 0.2971 -0.0258 0.4335 11.00000 0.05 0.14
Q15 1 0.3411 -0.4418 0.5174 11.00000 0.05 0.14
Q16 1 0.7188 0.3904 0.8623 11.00000 0.05 0.14
Q17 1 0.6814 0.5007 0.8004 11.00000 0.05 0.14
Q18 1 0.5595 1.1670 0.7768 11.00000 0.05 0.14
Q19 1 0.5207 0.1840 0.6190 11.00000 0.05 0.14
Q20 1 0.3868 -0.1569 0.6834 11.00000 0.05 0.14
;
_shelx_res_checksum 9702
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_PII_298K
_database_code_depnum_ccdc_archive 'CCDC 1957490'
loop_
_audit_author_name
_audit_author_address
'Tatiana Timofeeva'
;New Mexico Highlands University
United States of America
;
_audit_update_record
;
2019-10-03 deposited with the CCDC. 2019-10-14 downloaded from the CCDC.
;
_audit_creation_date 2019-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common ?
_chemical_name_systematic rac-3-phenylpyrrolidin-2,5-dione
_chemical_formula_moiety 'C10 H9 N O2'
_chemical_formula_sum 'C10 H9 N O2'
_chemical_formula_weight 175.18
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 15.57(4)
_cell_length_b 5.719(15)
_cell_length_c 20.69(6)
_cell_angle_alpha 90
_cell_angle_beta 107.77(2)
_cell_angle_gamma 90
_cell_volume 1754(8)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 773
_cell_measurement_temperature 298
_cell_measurement_theta_max 18.427
_cell_measurement_theta_min 3.710
_shelx_estimated_absorpt_T_max 0.987
_shelx_estimated_absorpt_T_min 0.970
_exptl_absorpt_coefficient_mu 0.094
_exptl_absorpt_correction_T_max 0.7443
_exptl_absorpt_correction_T_min 0.5908
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0692 before and 0.0442 after correction. The Ratio of minimum to maximum transmission is 0.7938. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.327
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plate
_exptl_crystal_F_000 736
_exptl_crystal_size_max 0.325
_exptl_crystal_size_mid 0.209
_exptl_crystal_size_min 0.136
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0414
_diffrn_reflns_av_unetI/netI 0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 5
_diffrn_reflns_limit_k_min -5
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_number 4381
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full 18.748
_diffrn_reflns_theta_max 18.748
_diffrn_reflns_theta_min 2.067
_diffrn_ambient_temperature 298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 971
_reflns_number_total 1331
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT V8.38A (?, 2016)'
_computing_data_collection ?
_computing_data_reduction 'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'XS (Sheldrick, 2008)'
_refine_diff_density_max 0.109
_refine_diff_density_min -0.179
_refine_diff_density_rms 0.032
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.988
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 235
_refine_ls_number_reflns 1331
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0581
_refine_ls_R_factor_gt 0.0368
_refine_ls_restrained_S_all 0.988
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0576P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0846
_refine_ls_wR_factor_ref 0.0950
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
C3(H3), C3A(H3A)
2.b Secondary CH2 refined with riding coordinates:
C2(H2A,H2B), C2A(H2AA,H2AB)
2.c Aromatic/amide H refined with riding coordinates:
N1(H1), N1A(H1A), C10(H10), C10A(H10A), C9(H9), C9A(H9A), C8(H8), C8A(H8A),
C7(H7), C7A(H7A), C6(H6), C6A(H6A)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5721(2) -0.1730(4) 0.55814(14) 0.0627(9) Uani 1 1 d . . . . .
O1A O 0.58691(17) 0.0202(5) 0.77220(14) 0.0583(8) Uani 1 1 d . . . . .
O2 O 0.34077(19) 0.1416(5) 0.61810(14) 0.0692(9) Uani 1 1 d . . . . .
O2A O 0.60888(15) -0.6403(5) 0.65675(14) 0.0583(8) Uani 1 1 d . . . . .
N1 N 0.4686(3) 0.0152(5) 0.59752(16) 0.0497(9) Uani 1 1 d . . . . .
H1 H 0.503395 0.126186 0.618352 0.060 Uiso 1 1 calc R . . . .
N1A N 0.58296(19) -0.3334(6) 0.71900(16) 0.0450(9) Uani 1 1 d . . . . .
H1A H 0.531291 -0.379150 0.721199 0.054 Uiso 1 1 calc R . . . .
C4 C 0.3809(3) -0.0031(8) 0.5963(2) 0.0512(12) Uani 1 1 d . . . . .
C4A C 0.6336(2) -0.4611(8) 0.6883(2) 0.0448(11) Uani 1 1 d . . . . .
C1 C 0.4967(3) -0.1568(7) 0.5630(2) 0.0489(11) Uani 1 1 d . . . . .
C1A C 0.6218(3) -0.1260(7) 0.7460(2) 0.0440(11) Uani 1 1 d . . . . .
C2 C 0.4180(2) -0.3107(6) 0.5320(2) 0.0575(12) Uani 1 1 d . . . . .
H2A H 0.433997 -0.473766 0.541502 0.069 Uiso 1 1 calc R . . . .
H2B H 0.396066 -0.288684 0.483191 0.069 Uiso 1 1 calc R . . . .
C2A C 0.7113(2) -0.1110(6) 0.7350(2) 0.0586(12) Uani 1 1 d . . . . .
H2AA H 0.758590 -0.094793 0.777888 0.070 Uiso 1 1 calc R . . . .
H2AB H 0.713647 0.022334 0.706576 0.070 Uiso 1 1 calc R . . . .
C3 C 0.3466(2) -0.2361(6) 0.5649(2) 0.0476(11) Uani 1 1 d . . . . .
H3 H 0.349788 -0.345540 0.601967 0.057 Uiso 1 1 calc R . . . .
C3A C 0.7228(2) -0.3393(6) 0.6998(2) 0.0460(11) Uani 1 1 d . . . . .
H3A H 0.730565 -0.302107 0.655659 0.055 Uiso 1 1 calc R . . . .
C5 C 0.2512(3) -0.2324(7) 0.5199(2) 0.0484(11) Uani 1 1 d . . . . .
C5A C 0.7990(2) -0.4941(6) 0.7386(2) 0.0399(10) Uani 1 1 d . . . . .
C10 C 0.1953(3) -0.4182(7) 0.5211(2) 0.0646(13) Uani 1 1 d . . . . .
H10 H 0.217419 -0.545241 0.549352 0.078 Uiso 1 1 calc R . . . .
C10A C 0.8491(2) -0.6120(7) 0.7047(2) 0.0484(11) Uani 1 1 d . . . . .
H10A H 0.836871 -0.589551 0.658257 0.058 Uiso 1 1 calc R . . . .
C9 C 0.1070(4) -0.4162(10) 0.4805(3) 0.0835(15) Uani 1 1 d . . . . .
H9 H 0.069966 -0.544064 0.480297 0.100 Uiso 1 1 calc R . . . .
C9A C 0.9169(3) -0.7622(7) 0.7381(3) 0.0626(12) Uani 1 1 d . . . . .
H9A H 0.949996 -0.840988 0.714281 0.075 Uiso 1 1 calc R . . . .
C8 C 0.0740(3) -0.2297(13) 0.4412(3) 0.0900(18) Uani 1 1 d . . . . .
H8 H 0.013325 -0.225454 0.415992 0.108 Uiso 1 1 calc R . . . .
C8A C 0.9355(3) -0.7952(7) 0.8056(3) 0.0632(13) Uani 1 1 d . . . . .
H8A H 0.981529 -0.896569 0.828240 0.076 Uiso 1 1 calc R . . . .
C7 C 0.1287(4) -0.0466(9) 0.4379(3) 0.0942(18) Uani 1 1 d . . . . .
H7 H 0.106112 0.078753 0.409125 0.113 Uiso 1 1 calc R . . . .
C7A C 0.8870(3) -0.6807(8) 0.8408(2) 0.0683(13) Uani 1 1 d . . . . .
H7A H 0.900476 -0.703085 0.887317 0.082 Uiso 1 1 calc R . . . .
C6 C 0.2171(3) -0.0487(7) 0.4773(2) 0.0722(14) Uani 1 1 d . . . . .
H6 H 0.254503 0.075974 0.475112 0.087 Uiso 1 1 calc R . . . .
C6A C 0.8178(3) -0.5313(7) 0.8072(3) 0.0573(12) Uani 1 1 d . . . . .
H6A H 0.784023 -0.455867 0.831044 0.069 Uiso 1 1 calc R . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.051(2) 0.0636(19) 0.070(2) 0.0093(15) 0.0137(17) 0.0084(15)
O1A 0.0536(18) 0.0505(18) 0.071(2) 0.0003(16) 0.0188(15) 0.0132(15)
O2 0.068(2) 0.069(2) 0.068(2) -0.0208(17) 0.0174(16) 0.0020(16)
O2A 0.0554(18) 0.0365(17) 0.075(2) -0.0061(16) 0.0074(14) -0.0044(14)
N1 0.053(3) 0.040(2) 0.047(2) -0.0021(18) 0.0018(18) -0.0032(18)
N1A 0.0323(19) 0.044(2) 0.055(2) 0.0066(18) 0.0070(17) -0.0049(19)
C4 0.048(3) 0.054(3) 0.046(3) 0.002(2) 0.006(2) 0.000(2)
C4A 0.036(3) 0.039(3) 0.058(3) 0.014(2) 0.014(2) 0.009(3)
C1 0.053(3) 0.038(3) 0.049(3) 0.011(2) 0.005(3) 0.008(3)
C1A 0.037(3) 0.036(3) 0.055(3) 0.012(2) 0.009(2) 0.008(2)
C2 0.057(3) 0.042(2) 0.070(3) -0.003(2) 0.013(3) 0.002(2)
C2A 0.044(3) 0.036(2) 0.097(4) -0.004(2) 0.023(2) 0.0004(19)
C3 0.049(3) 0.044(3) 0.046(3) 0.003(2) 0.008(2) -0.008(2)
C3A 0.040(3) 0.036(2) 0.065(3) 0.006(2) 0.020(2) 0.005(2)
C5 0.051(3) 0.042(3) 0.050(3) -0.007(2) 0.013(2) -0.005(2)
C5A 0.036(2) 0.031(2) 0.055(4) -0.003(2) 0.018(2) -0.003(2)
C10 0.055(3) 0.068(3) 0.070(4) -0.012(2) 0.017(3) -0.005(3)
C10A 0.040(3) 0.050(2) 0.053(3) 0.004(2) 0.010(3) 0.008(2)
C9 0.075(4) 0.080(4) 0.098(4) -0.031(4) 0.031(3) -0.021(3)
C9A 0.058(3) 0.058(3) 0.073(4) 0.002(3) 0.020(3) 0.015(2)
C8 0.056(3) 0.104(4) 0.099(5) -0.046(4) 0.008(3) 0.008(4)
C8A 0.046(3) 0.050(3) 0.082(5) 0.009(3) 0.004(3) 0.004(2)
C7 0.090(4) 0.074(4) 0.087(4) -0.019(3) -0.019(4) 0.019(3)
C7A 0.061(3) 0.080(3) 0.055(3) 0.011(3) 0.006(3) -0.003(3)
C6 0.076(4) 0.055(3) 0.065(3) -0.003(3) -0.009(3) -0.003(3)
C6A 0.054(3) 0.062(3) 0.057(4) 0.001(3) 0.018(2) 0.003(2)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.213(5) . ?
O1A C1A 1.211(5) . ?
O2 C4 1.204(5) . ?
O2A C4A 1.213(5) . ?
N1 H1 0.8600 . ?
N1 C4 1.361(6) . ?
N1 C1 1.364(5) . ?
N1A H1A 0.8600 . ?
N1A C4A 1.365(5) . ?
N1A C1A 1.371(5) . ?
C4 C3 1.507(6) . ?
C4A C3A 1.505(6) . ?
C1 C2 1.485(6) . ?
C1A C2A 1.482(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.530(6) . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C2A C3A 1.531(6) . ?
C3 H3 0.9800 . ?
C3 C5 1.492(6) . ?
C3A H3A 0.9800 . ?
C3A C5A 1.501(5) . ?
C5 C10 1.378(6) . ?
C5 C6 1.370(6) . ?
C5A C10A 1.375(5) . ?
C5A C6A 1.375(6) . ?
C10 H10 0.9300 . ?
C10 C9 1.375(6) . ?
C10A H10A 0.9300 . ?
C10A C9A 1.372(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.345(7) . ?
C9A H9A 0.9300 . ?
C9A C8A 1.350(7) . ?
C8 H8 0.9300 . ?
C8 C7 1.364(7) . ?
C8A H8A 0.9300 . ?
C8A C7A 1.365(6) . ?
C7 H7 0.9300 . ?
C7 C6 1.369(6) . ?
C7A H7A 0.9300 . ?
C7A C6A 1.384(6) . ?
C6 H6 0.9300 . ?
C6A H6A 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 H1 122.8 . . ?
C4 N1 C1 114.5(4) . . ?
C1 N1 H1 122.8 . . ?
C4A N1A H1A 123.0 . . ?
C4A N1A C1A 114.0(4) . . ?
C1A N1A H1A 123.0 . . ?
O2 C4 N1 124.9(4) . . ?
O2 C4 C3 127.8(4) . . ?
N1 C4 C3 107.3(4) . . ?
O2A C4A N1A 124.7(4) . . ?
O2A C4A C3A 127.0(4) . . ?
N1A C4A C3A 108.3(4) . . ?
O1 C1 N1 124.9(4) . . ?
O1 C1 C2 127.6(4) . . ?
N1 C1 C2 107.4(4) . . ?
O1A C1A N1A 125.3(4) . . ?
O1A C1A C2A 126.9(4) . . ?
N1A C1A C2A 107.8(4) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C1 C2 C3 104.9(4) . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C1A C2A H2AA 110.5 . . ?
C1A C2A H2AB 110.5 . . ?
C1A C2A C3A 106.0(3) . . ?
H2AA C2A H2AB 108.7 . . ?
C3A C2A H2AA 110.5 . . ?
C3A C2A H2AB 110.5 . . ?
C4 C3 C2 103.2(3) . . ?
C4 C3 H3 107.5 . . ?
C2 C3 H3 107.5 . . ?
C5 C3 C4 114.2(3) . . ?
C5 C3 C2 116.5(4) . . ?
C5 C3 H3 107.5 . . ?
C4A C3A C2A 103.5(3) . . ?
C4A C3A H3A 108.9 . . ?
C2A C3A H3A 108.9 . . ?
C5A C3A C4A 110.6(3) . . ?
C5A C3A C2A 115.9(3) . . ?
C5A C3A H3A 108.9 . . ?
C10 C5 C3 119.4(4) . . ?
C6 C5 C3 121.9(4) . . ?
C6 C5 C10 118.7(4) . . ?
C10A C5A C3A 119.7(4) . . ?
C10A C5A C6A 118.3(4) . . ?
C6A C5A C3A 121.9(4) . . ?
C5 C10 H10 119.9 . . ?
C9 C10 C5 120.1(4) . . ?
C9 C10 H10 119.9 . . ?
C5A C10A H10A 119.3 . . ?
C9A C10A C5A 121.3(4) . . ?
C9A C10A H10A 119.3 . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.1(4) . . ?
C8 C9 H9 119.9 . . ?
C10A C9A H9A 120.1 . . ?
C8A C9A C10A 119.8(4) . . ?
C8A C9A H9A 120.1 . . ?
C9 C8 H8 119.7 . . ?
C9 C8 C7 120.7(5) . . ?
C7 C8 H8 119.7 . . ?
C9A C8A H8A 119.8 . . ?
C9A C8A C7A 120.4(4) . . ?
C7A C8A H8A 119.8 . . ?
C8 C7 H7 120.2 . . ?
C8 C7 C6 119.5(5) . . ?
C6 C7 H7 120.2 . . ?
C8A C7A H7A 120.0 . . ?
C8A C7A C6A 120.0(5) . . ?
C6A C7A H7A 120.0 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 H6 119.6 . . ?
C5A C6A C7A 120.1(4) . . ?
C5A C6A H6A 119.9 . . ?
C7A C6A H6A 119.9 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1A H1A O1A 0.86 1.97 2.832(8) 178.8 2_646 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 170.3(4) . . . . ?
O1A C1A C2A C3A -179.5(4) . . . . ?
O2 C4 C3 C2 166.6(4) . . . . ?
O2 C4 C3 C5 39.2(6) . . . . ?
O2A C4A C3A C2A 173.5(4) . . . . ?
O2A C4A C3A C5A -61.8(5) . . . . ?
N1 C4 C3 C2 -14.9(4) . . . . ?
N1 C4 C3 C5 -142.4(4) . . . . ?
N1 C1 C2 C3 -11.4(4) . . . . ?
N1A C4A C3A C2A -5.8(4) . . . . ?
N1A C4A C3A C5A 118.9(4) . . . . ?
N1A C1A C2A C3A -1.7(4) . . . . ?
C4 N1 C1 O1 -179.7(3) . . . . ?
C4 N1 C1 C2 1.9(4) . . . . ?
C4 C3 C5 C10 -140.7(4) . . . . ?
C4 C3 C5 C6 39.2(5) . . . . ?
C4A N1A C1A O1A 175.7(4) . . . . ?
C4A N1A C1A C2A -2.2(4) . . . . ?
C4A C3A C5A C10A 101.2(4) . . . . ?
C4A C3A C5A C6A -75.6(4) . . . . ?
C1 N1 C4 O2 -172.8(4) . . . . ?
C1 N1 C4 C3 8.7(4) . . . . ?
C1 C2 C3 C4 15.7(4) . . . . ?
C1 C2 C3 C5 141.7(3) . . . . ?
C1A N1A C4A O2A -174.1(3) . . . . ?
C1A N1A C4A C3A 5.2(4) . . . . ?
C1A C2A C3A C4A 4.4(4) . . . . ?
C1A C2A C3A C5A -116.7(4) . . . . ?
C2 C3 C5 C10 99.0(4) . . . . ?
C2 C3 C5 C6 -81.1(5) . . . . ?
C2A C3A C5A C10A -141.5(3) . . . . ?
C2A C3A C5A C6A 41.7(5) . . . . ?
C3 C5 C10 C9 179.3(4) . . . . ?
C3 C5 C6 C7 -178.2(4) . . . . ?
C3A C5A C10A C9A -177.4(3) . . . . ?
C3A C5A C6A C7A 178.1(3) . . . . ?
C5 C10 C9 C8 -2.1(7) . . . . ?
C5A C10A C9A C8A -0.3(6) . . . . ?
C10 C5 C6 C7 1.7(6) . . . . ?
C10 C9 C8 C7 3.9(7) . . . . ?
C10A C5A C6A C7A 1.3(5) . . . . ?
C10A C9A C8A C7A 0.2(6) . . . . ?
C9 C8 C7 C6 -2.8(8) . . . . ?
C9A C8A C7A C6A 0.6(6) . . . . ?
C8 C7 C6 C5 0.0(7) . . . . ?
C8A C7A C6A C5A -1.3(6) . . . . ?
C6 C5 C10 C9 -0.6(6) . . . . ?
C6A C5A C10A C9A -0.5(5) . . . . ?
_shelx_res_file
;
TITL polyII in P21/c #14
polyii.res
created by SHELXL-2017/1 at 12:10:14 on 24-Sep-2019
REM reset to P21/c #14
CELL 0.71073 15.5654 5.7185 20.6907 90 107.7736 90
ZERR 8 0.0416 0.0153 0.0556 0 0.0244 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 80 72 8 16
EQIV $1 1-X,-0.5+Y,1.5-Z
L.S. 10
PLAN 20
SIZE 0.136 0.209 0.325
TEMP 24.85
HTAB N1A O1A_$1
BOND
BOND $H
CONF
fmap 2
acta
OMIT -6 1 5
REM
REM
REM
WGHT 0.057600
FVAR 0.17461
O1 4 0.572110 -0.173022 0.558140 11.00000 0.05107 0.06365 =
0.07029 0.00935 0.01374 0.00845
O1A 4 0.586906 0.020242 0.772195 11.00000 0.05356 0.05052 =
0.07062 0.00031 0.01881 0.01317
O2 4 0.340774 0.141562 0.618104 11.00000 0.06828 0.06938 =
0.06759 -0.02076 0.01738 0.00200
O2A 4 0.608881 -0.640336 0.656754 11.00000 0.05541 0.03654 =
0.07451 -0.00610 0.00741 -0.00436
N1 3 0.468575 0.015223 0.597516 11.00000 0.05305 0.03956 =
0.04750 -0.00205 0.00184 -0.00324
AFIX 43
H1 2 0.503395 0.126186 0.618352 11.00000 -1.20000
AFIX 0
N1A 3 0.582965 -0.333445 0.719005 11.00000 0.03228 0.04409 =
0.05452 0.00662 0.00703 -0.00487
AFIX 43
H1A 2 0.531291 -0.379150 0.721199 11.00000 -1.20000
AFIX 0
C4 1 0.380880 -0.003113 0.596263 11.00000 0.04823 0.05434 =
0.04571 0.00171 0.00630 0.00006
C4A 1 0.633599 -0.461066 0.688282 11.00000 0.03592 0.03938 =
0.05845 0.01392 0.01365 0.00920
C1 1 0.496658 -0.156846 0.563011 11.00000 0.05325 0.03779 =
0.04886 0.01116 0.00531 0.00758
C1A 1 0.621778 -0.126023 0.746042 11.00000 0.03720 0.03622 =
0.05510 0.01250 0.00910 0.00788
C2 1 0.417962 -0.310676 0.531978 11.00000 0.05652 0.04160 =
0.07041 -0.00343 0.01340 0.00188
AFIX 23
H2A 2 0.433997 -0.473766 0.541502 11.00000 -1.20000
H2B 2 0.396066 -0.288684 0.483191 11.00000 -1.20000
AFIX 0
C2A 1 0.711266 -0.111018 0.734952 11.00000 0.04425 0.03552 =
0.09698 -0.00358 0.02283 0.00038
AFIX 23
H2AA 2 0.758590 -0.094793 0.777888 11.00000 -1.20000
H2AB 2 0.713647 0.022334 0.706576 11.00000 -1.20000
AFIX 0
C3 1 0.346592 -0.236090 0.564859 11.00000 0.04869 0.04409 =
0.04572 0.00272 0.00785 -0.00770
AFIX 13
H3 2 0.349788 -0.345540 0.601967 11.00000 -1.20000
AFIX 0
C3A 1 0.722759 -0.339250 0.699766 11.00000 0.04008 0.03637 =
0.06451 0.00636 0.02047 0.00490
AFIX 13
H3A 2 0.730565 -0.302107 0.655659 11.00000 -1.20000
AFIX 0
C5 1 0.251233 -0.232375 0.519921 11.00000 0.05142 0.04225 =
0.04988 -0.00723 0.01283 -0.00450
C5A 1 0.798956 -0.494088 0.738580 11.00000 0.03561 0.03137 =
0.05546 -0.00259 0.01776 -0.00281
C10 1 0.195339 -0.418239 0.521086 11.00000 0.05546 0.06774 =
0.06964 -0.01192 0.01744 -0.00541
AFIX 43
H10 2 0.217419 -0.545241 0.549352 11.00000 -1.20000
AFIX 0
C10A 1 0.849126 -0.612012 0.704714 11.00000 0.03956 0.05026 =
0.05292 0.00361 0.01034 0.00751
AFIX 43
H10A 2 0.836871 -0.589551 0.658257 11.00000 -1.20000
AFIX 0
C9 1 0.106987 -0.416215 0.480529 11.00000 0.07482 0.08007 =
0.09839 -0.03075 0.03064 -0.02101
AFIX 43
H9 2 0.069966 -0.544064 0.480297 11.00000 -1.20000
AFIX 0
C9A 1 0.916929 -0.762207 0.738073 11.00000 0.05781 0.05763 =
0.07265 0.00169 0.02024 0.01471
AFIX 43
H9A 2 0.949996 -0.840988 0.714281 11.00000 -1.20000
AFIX 0
C8 1 0.074039 -0.229697 0.441211 11.00000 0.05618 0.10441 =
0.09898 -0.04581 0.00837 0.00844
AFIX 43
H8 2 0.013325 -0.225454 0.415992 11.00000 -1.20000
AFIX 0
C8A 1 0.935457 -0.795189 0.805581 11.00000 0.04627 0.05045 =
0.08231 0.00946 0.00372 0.00356
AFIX 43
H8A 2 0.981529 -0.896569 0.828240 11.00000 -1.20000
AFIX 0
C7 1 0.128736 -0.046611 0.437924 11.00000 0.09045 0.07446 =
0.08674 -0.01927 -0.01876 0.01862
AFIX 43
H7 2 0.106112 0.078753 0.409125 11.00000 -1.20000
AFIX 0
C7A 1 0.887004 -0.680697 0.840762 11.00000 0.06138 0.07990 =
0.05542 0.01107 0.00561 -0.00304
AFIX 43
H7A 2 0.900476 -0.703085 0.887317 11.00000 -1.20000
AFIX 0
C6 1 0.217142 -0.048727 0.477308 11.00000 0.07644 0.05510 =
0.06486 -0.00305 -0.00857 -0.00311
AFIX 43
H6 2 0.254503 0.075974 0.475112 11.00000 -1.20000
AFIX 0
C6A 1 0.817815 -0.531261 0.807180 11.00000 0.05403 0.06200 =
0.05656 0.00085 0.01800 0.00335
AFIX 43
H6A 2 0.784023 -0.455867 0.831044 11.00000 -1.20000
AFIX 0
HKLF 4
REM polyII in P21/c #14
REM R1 = 0.0368 for 971 Fo > 4sig(Fo) and 0.0581 for all 1331 data
REM 235 parameters refined using 0 restraints
END
WGHT 0.0576 0.0000
REM Highest difference peak 0.109, deepest hole -0.179, 1-sigma level 0.032
Q1 1 0.6136 -0.4788 0.6039 11.00000 0.05 0.11
Q2 1 0.7450 -0.3807 0.6366 11.00000 0.05 0.11
Q3 1 0.9082 -0.9046 0.9193 11.00000 0.05 0.10
Q4 1 0.8392 -0.7478 0.9032 11.00000 0.05 0.10
Q5 1 0.3669 0.1717 0.5217 11.00000 0.05 0.10
Q6 1 0.9068 -1.0639 0.7039 11.00000 0.05 0.09
Q7 1 0.6802 0.0640 0.6442 11.00000 0.05 0.09
Q8 1 0.5966 -0.5820 0.7776 11.00000 0.05 0.09
Q9 1 0.3212 0.2224 0.4539 11.00000 0.05 0.09
Q10 1 0.7142 -0.6555 0.8389 11.00000 0.05 0.09
Q11 1 0.5336 -0.3966 0.6017 11.00000 0.05 0.08
Q12 1 1.0584 -0.8554 0.8053 11.00000 0.05 0.08
Q13 1 0.1337 -0.5755 0.5643 11.00000 0.05 0.08
Q14 1 0.3170 -0.4481 0.4421 11.00000 0.05 0.08
Q15 1 0.6327 -0.2253 0.6243 11.00000 0.05 0.08
Q16 1 0.5355 -0.1126 0.7833 11.00000 0.05 0.08
Q17 1 0.6577 -0.0075 0.5974 11.00000 0.05 0.08
Q18 1 0.6626 -0.7442 0.6210 11.00000 0.05 0.08
Q19 1 0.4969 -0.5444 0.5861 11.00000 0.05 0.08
Q20 1 0.6728 -0.4276 0.8019 11.00000 0.05 0.08
;
_shelx_res_checksum 29457
_olex2_exptl_crystal_mounting_method 'Single plate was mounted on nylon loop'
_olex2_submission_original_sample_id AVK14A
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_avk14a
_database_code_depnum_ccdc_archive 'CCDC 1888876'
loop_
_audit_author_name
_audit_author_address
'Boris Averkiev'
;New Mexico Highlands University
United States of America
;
_audit_update_record
;
2019-01-08 deposited with the CCDC. 2019-10-14 downloaded from the CCDC.
;
_audit_creation_method SHELXL-2014/7
_shelx_SHELXL_version_number 2014/7
_chemical_name_systematic 3-phenylpyrrolidine-2,5-dione
_chemical_name_common ?
_chemical_melting_point 353.2
_chemical_formula_moiety 'C10 H9 N O2'
_chemical_formula_sum 'C10 H9 N O2'
_chemical_formula_weight 175.18
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 21/c'
_space_group_name_Hall '-P 2ybc'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 15.564(5)
_cell_length_b 5.7158(19)
_cell_length_c 20.595(8)
_cell_angle_alpha 90
_cell_angle_beta 107.363(6)
_cell_angle_gamma 90
_cell_volume 1748.6(10)
_cell_formula_units_Z 8
_cell_measurement_temperature 215(2)
_cell_measurement_reflns_used 3776
_cell_measurement_theta_min 3.71
_cell_measurement_theta_max 25.38
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.331
_exptl_crystal_F_000 736
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.200
_exptl_crystal_size_mid 0.100
_exptl_crystal_size_min 0.100
_exptl_absorpt_coefficient_mu 0.094
_shelx_estimated_absorpt_T_min 0.981
_shelx_estimated_absorpt_T_max 0.991
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.6544
_exptl_absorpt_correction_T_max 0.7460
_exptl_absorpt_process_details
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_exptl_absorpt_special_details ?
_diffrn_ambient_temperature 215(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source ?
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 22399
_diffrn_reflns_av_unetI/netI 0.0441
_diffrn_reflns_av_R_equivalents 0.0566
_diffrn_reflns_limit_h_min -20
_diffrn_reflns_limit_h_max 20
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_l_min -27
_diffrn_reflns_limit_l_max 27
_diffrn_reflns_theta_min 2.072
_diffrn_reflns_theta_max 28.071
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total 4257
_reflns_number_gt 2869
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_max .
_reflns_Friedel_fraction_full .
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection 'Bruker APEX2'
_computing_cell_refinement 'Bruker SAINT'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_refine_special_details ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+0.2610P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary difmap
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens difmap
_refine_ls_hydrogen_treatment refall
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_number_reflns 4257
_refine_ls_number_parameters 307
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0757
_refine_ls_R_factor_gt 0.0429
_refine_ls_wR_factor_ref 0.0993
_refine_ls_wR_factor_gt 0.0867
_refine_ls_goodness_of_fit_ref 1.017
_refine_ls_restrained_S_all 1.017
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.60947(7) 0.13738(17) 0.15603(5) 0.0379(3) Uani 1 1 d . . . . .
O2A O 0.58707(7) -0.52514(19) 0.27223(5) 0.0375(3) Uani 1 1 d . . . . .
N1A N 0.58340(8) -0.1702(2) 0.21925(6) 0.0283(3) Uani 1 1 d . . . . .
H1A H 0.5310(11) -0.126(3) 0.2215(8) 0.034(4) Uiso 1 1 d . . . . .
C1A C 0.63389(9) -0.0423(2) 0.18786(7) 0.0272(3) Uani 1 1 d . . . . .
C2A C 0.72391(9) -0.1648(2) 0.19905(8) 0.0291(3) Uani 1 1 d . . . . .
H2A H 0.7303(10) -0.195(3) 0.1535(8) 0.030(4) Uiso 1 1 d . . . . .
C3A C 0.71235(11) -0.3931(3) 0.23419(11) 0.0399(4) Uani 1 1 d . . . . .
H3AA H 0.7570(13) -0.418(3) 0.2751(10) 0.055(6) Uiso 1 1 d . . . . .
H3AB H 0.7120(12) -0.526(3) 0.2053(9) 0.059(6) Uiso 1 1 d . . . . .
C4A C 0.62242(9) -0.3785(2) 0.24596(7) 0.0277(3) Uani 1 1 d . . . . .
C5A C 0.79995(9) -0.0061(2) 0.23811(7) 0.0261(3) Uani 1 1 d . . . . .
C6A C 0.85061(10) 0.1136(3) 0.20382(8) 0.0326(3) Uani 1 1 d . . . . .
H6A H 0.8379(11) 0.093(3) 0.1544(9) 0.044(5) Uiso 1 1 d . . . . .
C7A C 0.91872(11) 0.2651(3) 0.23834(9) 0.0409(4) Uani 1 1 d . . . . .
H7A H 0.9539(13) 0.344(3) 0.2131(9) 0.058(5) Uiso 1 1 d . . . . .
C8A C 0.93692(11) 0.2968(3) 0.30703(9) 0.0437(4) Uani 1 1 d . . . . .
H8A H 0.9855(13) 0.402(3) 0.3310(9) 0.055(5) Uiso 1 1 d . . . . .
C9A C 0.88729(11) 0.1792(3) 0.34165(9) 0.0454(4) Uani 1 1 d . . . . .
H9A H 0.9008(13) 0.202(4) 0.3911(11) 0.072(6) Uiso 1 1 d . . . . .
C10A C 0.81889(11) 0.0291(3) 0.30759(8) 0.0378(4) Uani 1 1 d . . . . .
H10A H 0.7813(11) -0.049(3) 0.3303(8) 0.044(5) Uiso 1 1 d . . . . .
O1B O 0.34038(8) 0.3536(2) 0.11826(6) 0.0463(3) Uani 1 1 d . . . . .
O2B O 0.57301(7) 0.6713(2) 0.05819(5) 0.0409(3) Uani 1 1 d . . . . .
N1B N 0.46956(9) 0.4810(2) 0.09824(6) 0.0328(3) Uani 1 1 d . . . . .
H1B H 0.5061(12) 0.361(3) 0.1193(9) 0.053(5) Uiso 1 1 d . . . . .
C1B C 0.38106(10) 0.4998(3) 0.09657(7) 0.0321(3) Uani 1 1 d . . . . .
C2B C 0.34684(10) 0.7360(3) 0.06516(8) 0.0328(3) Uani 1 1 d . . . . .
H2B H 0.3516(10) 0.839(3) 0.1020(8) 0.032(4) Uiso 1 1 d . . . . .
C3B C 0.41790(11) 0.8109(3) 0.03156(9) 0.0371(4) Uani 1 1 d . . . . .
H3BA H 0.4355(12) 0.973(3) 0.0376(8) 0.049(5) Uiso 1 1 d . . . . .
H3BB H 0.3985(11) 0.777(3) -0.0181(9) 0.049(5) Uiso 1 1 d . . . . .
C4B C 0.49745(10) 0.6557(3) 0.06281(7) 0.0318(3) Uani 1 1 d . . . . .
C5B C 0.25041(10) 0.7331(3) 0.02015(7) 0.0333(3) Uani 1 1 d . . . . .
C6B C 0.19471(11) 0.9210(3) 0.02108(9) 0.0423(4) Uani 1 1 d . . . . .
H6B H 0.2184(12) 1.049(3) 0.0511(9) 0.053(5) Uiso 1 1 d . . . . .
C7B C 0.10550(13) 0.9198(4) -0.01933(11) 0.0549(5) Uani 1 1 d . . . . .
H7B H 0.0679(14) 1.053(4) -0.0182(10) 0.064(6) Uiso 1 1 d . . . . .
C8B C 0.07177(13) 0.7301(4) -0.05988(11) 0.0602(6) Uani 1 1 d . . . . .
H8B H 0.0106(15) 0.728(3) -0.0867(11) 0.071(6) Uiso 1 1 d . . . . .
C9B C 0.12709(14) 0.5451(4) -0.06190(11) 0.0620(6) Uani 1 1 d . . . . .
H9B H 0.1053(15) 0.417(4) -0.0906(11) 0.076(7) Uiso 1 1 d . . . . .
C10B C 0.21650(13) 0.5462(3) -0.02267(9) 0.0491(5) Uani 1 1 d . . . . .
H10B H 0.2555(13) 0.413(4) -0.0253(9) 0.064(6) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1A 0.0363(6) 0.0279(6) 0.0442(6) 0.0025(5) 0.0041(5) 0.0044(5)
O2A 0.0338(6) 0.0386(6) 0.0411(6) 0.0006(5) 0.0125(5) -0.0091(5)
N1A 0.0193(6) 0.0318(7) 0.0331(7) -0.0038(5) 0.0070(5) 0.0025(5)
C1A 0.0246(7) 0.0236(7) 0.0300(7) -0.0067(6) 0.0032(6) -0.0008(6)
C2A 0.0245(7) 0.0232(7) 0.0410(9) -0.0033(6) 0.0121(6) -0.0016(6)
C3A 0.0271(8) 0.0229(8) 0.0713(13) 0.0048(8) 0.0170(8) 0.0017(6)
C4A 0.0236(7) 0.0279(7) 0.0298(8) -0.0058(6) 0.0051(6) -0.0046(6)
C5A 0.0207(7) 0.0217(6) 0.0354(8) 0.0003(6) 0.0076(6) 0.0028(5)
C6A 0.0304(8) 0.0312(8) 0.0371(9) -0.0007(7) 0.0112(7) -0.0029(6)
C7A 0.0311(8) 0.0370(9) 0.0564(11) -0.0019(8) 0.0158(8) -0.0099(7)
C8A 0.0291(8) 0.0399(9) 0.0556(11) -0.0114(8) 0.0026(8) -0.0042(7)
C9A 0.0390(9) 0.0570(11) 0.0352(9) -0.0088(8) 0.0031(7) 0.0025(8)
C10A 0.0341(9) 0.0449(10) 0.0359(9) 0.0022(7) 0.0127(7) 0.0004(7)
O1B 0.0455(7) 0.0508(7) 0.0426(7) 0.0180(6) 0.0131(5) -0.0016(6)
O2B 0.0316(6) 0.0446(7) 0.0443(7) -0.0053(5) 0.0080(5) -0.0042(5)
N1B 0.0326(7) 0.0315(7) 0.0295(7) 0.0019(6) 0.0019(5) 0.0023(6)
C1B 0.0343(8) 0.0367(8) 0.0221(7) 0.0004(6) 0.0034(6) 0.0003(7)
C2B 0.0355(8) 0.0307(8) 0.0292(8) -0.0042(7) 0.0052(6) 0.0023(6)
C3B 0.0381(9) 0.0281(8) 0.0437(10) 0.0040(7) 0.0100(7) -0.0010(7)
C4B 0.0345(8) 0.0294(8) 0.0281(8) -0.0070(6) 0.0039(6) -0.0041(6)
C5B 0.0333(8) 0.0334(8) 0.0324(8) 0.0074(6) 0.0084(6) 0.0011(6)
C6B 0.0402(10) 0.0416(9) 0.0469(10) 0.0090(8) 0.0156(8) 0.0052(8)
C7B 0.0390(10) 0.0636(13) 0.0650(13) 0.0262(11) 0.0197(9) 0.0125(10)
C8B 0.0355(10) 0.0745(15) 0.0608(12) 0.0341(11) -0.0005(9) -0.0088(10)
C9B 0.0600(13) 0.0517(12) 0.0538(12) 0.0150(10) -0.0143(10) -0.0136(10)
C10B 0.0524(11) 0.0382(10) 0.0438(10) 0.0032(8) -0.0055(8) 0.0001(9)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C1A 1.2169(17) . ?
O2A C4A 1.2149(17) . ?
N1A C1A 1.3682(19) . ?
N1A C4A 1.3748(19) . ?
N1A H1A 0.868(17) . ?
C1A C2A 1.521(2) . ?
C2A C5A 1.517(2) . ?
C2A C3A 1.528(2) . ?
C2A H2A 0.988(15) . ?
C3A C4A 1.492(2) . ?
C3A H3AA 0.929(19) . ?
C3A H3AB 0.96(2) . ?
C5A C6A 1.386(2) . ?
C5A C10A 1.387(2) . ?
C6A C7A 1.389(2) . ?
C6A H6A 0.985(17) . ?
C7A C8A 1.369(3) . ?
C7A H7A 0.972(19) . ?
C8A C9A 1.373(3) . ?
C8A H8A 0.977(19) . ?
C9A C10A 1.384(2) . ?
C9A H9A 0.99(2) . ?
C10A H10A 0.960(17) . ?
O1B C1B 1.2114(18) . ?
O2B C4B 1.2110(18) . ?
N1B C1B 1.372(2) . ?
N1B C4B 1.381(2) . ?
N1B H1B 0.914(19) . ?
C1B C2B 1.523(2) . ?
C2B C5B 1.511(2) . ?
C2B C3B 1.530(2) . ?
C2B H2B 0.945(15) . ?
C3B C4B 1.503(2) . ?
C3B H3BA 0.963(18) . ?
C3B H3BB 0.996(18) . ?
C5B C6B 1.384(2) . ?
C5B C10B 1.385(2) . ?
C6B C7B 1.390(3) . ?
C6B H6B 0.956(19) . ?
C7B C8B 1.373(3) . ?
C7B H7B 0.97(2) . ?
C8B C9B 1.372(3) . ?
C8B H8B 0.95(2) . ?
C9B C10B 1.385(3) . ?
C9B H9B 0.94(2) . ?
C10B H10B 0.98(2) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A N1A C4A 113.84(12) . . ?
C1A N1A H1A 123.5(10) . . ?
C4A N1A H1A 122.6(10) . . ?
O1A C1A N1A 125.05(13) . . ?
O1A C1A C2A 126.55(13) . . ?
N1A C1A C2A 108.40(12) . . ?
C5A C2A C1A 110.03(11) . . ?
C5A C2A C3A 116.27(13) . . ?
C1A C2A C3A 103.38(11) . . ?
C5A C2A H2A 108.9(8) . . ?
C1A C2A H2A 106.6(8) . . ?
C3A C2A H2A 111.1(9) . . ?
C4A C3A C2A 106.13(12) . . ?
C4A C3A H3AA 110.2(12) . . ?
C2A C3A H3AA 113.5(12) . . ?
C4A C3A H3AB 108.1(11) . . ?
C2A C3A H3AB 111.2(11) . . ?
H3AA C3A H3AB 107.6(16) . . ?
O2A C4A N1A 124.83(13) . . ?
O2A C4A C3A 127.25(14) . . ?
N1A C4A C3A 107.88(12) . . ?
C6A C5A C10A 118.43(14) . . ?
C6A C5A C2A 119.82(13) . . ?
C10A C5A C2A 121.72(13) . . ?
C5A C6A C7A 120.68(16) . . ?
C5A C6A H6A 119.8(10) . . ?
C7A C6A H6A 119.5(10) . . ?
C8A C7A C6A 120.15(16) . . ?
C8A C7A H7A 121.0(11) . . ?
C6A C7A H7A 118.8(11) . . ?
C7A C8A C9A 119.78(16) . . ?
C7A C8A H8A 119.7(10) . . ?
C9A C8A H8A 120.6(10) . . ?
C8A C9A C10A 120.47(17) . . ?
C8A C9A H9A 119.5(12) . . ?
C10A C9A H9A 120.1(12) . . ?
C9A C10A C5A 120.48(15) . . ?
C9A C10A H10A 121.9(10) . . ?
C5A C10A H10A 117.5(10) . . ?
C1B N1B C4B 113.70(13) . . ?
C1B N1B H1B 123.3(11) . . ?
C4B N1B H1B 123.0(11) . . ?
O1B C1B N1B 124.63(14) . . ?
O1B C1B C2B 127.82(14) . . ?
N1B C1B C2B 107.53(13) . . ?
C5B C2B C1B 114.08(13) . . ?
C5B C2B C3B 116.44(13) . . ?
C1B C2B C3B 103.39(13) . . ?
C5B C2B H2B 109.0(9) . . ?
C1B C2B H2B 106.1(9) . . ?
C3B C2B H2B 107.2(9) . . ?
C4B C3B C2B 104.81(13) . . ?
C4B C3B H3BA 110.3(10) . . ?
C2B C3B H3BA 115.2(10) . . ?
C4B C3B H3BB 106.4(10) . . ?
C2B C3B H3BB 111.8(10) . . ?
H3BA C3B H3BB 107.9(14) . . ?
O2B C4B N1B 124.11(14) . . ?
O2B C4B C3B 128.16(15) . . ?
N1B C4B C3B 107.72(13) . . ?
C6B C5B C10B 119.08(16) . . ?
C6B C5B C2B 119.63(15) . . ?
C10B C5B C2B 121.29(14) . . ?
C5B C6B C7B 120.37(19) . . ?
C5B C6B H6B 118.6(11) . . ?
C7B C6B H6B 121.0(11) . . ?
C8B C7B C6B 120.04(19) . . ?
C8B C7B H7B 120.9(12) . . ?
C6B C7B H7B 119.0(12) . . ?
C9B C8B C7B 119.83(19) . . ?
C9B C8B H8B 120.1(13) . . ?
C7B C8B H8B 120.0(13) . . ?
C8B C9B C10B 120.6(2) . . ?
C8B C9B H9B 120.6(13) . . ?
C10B C9B H9B 118.8(14) . . ?
C9B C10B C5B 120.04(19) . . ?
C9B C10B H10B 119.5(11) . . ?
C5B C10B H10B 120.4(11) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4A N1A C1A O1A 173.71(13) . . . . ?
C4A N1A C1A C2A -5.63(15) . . . . ?
O1A C1A C2A C5A 62.00(19) . . . . ?
N1A C1A C2A C5A -118.67(13) . . . . ?
O1A C1A C2A C3A -173.18(15) . . . . ?
N1A C1A C2A C3A 6.15(16) . . . . ?
C5A C2A C3A C4A 116.06(15) . . . . ?
C1A C2A C3A C4A -4.60(17) . . . . ?
C1A N1A C4A O2A -175.30(13) . . . . ?
C1A N1A C4A C3A 2.50(17) . . . . ?
C2A C3A C4A O2A 179.39(14) . . . . ?
C2A C3A C4A N1A 1.66(18) . . . . ?
C1A C2A C5A C6A -101.59(15) . . . . ?
C3A C2A C5A C6A 141.38(14) . . . . ?
C1A C2A C5A C10A 76.40(17) . . . . ?
C3A C2A C5A C10A -40.64(19) . . . . ?
C10A C5A C6A C7A 0.0(2) . . . . ?
C2A C5A C6A C7A 178.05(14) . . . . ?
C5A C6A C7A C8A 0.4(2) . . . . ?
C6A C7A C8A C9A -0.3(3) . . . . ?
C7A C8A C9A C10A -0.1(3) . . . . ?
C8A C9A C10A C5A 0.5(3) . . . . ?
C6A C5A C10A C9A -0.4(2) . . . . ?
C2A C5A C10A C9A -178.43(14) . . . . ?
C4B N1B C1B O1B 172.22(14) . . . . ?
C4B N1B C1B C2B -9.49(16) . . . . ?
O1B C1B C2B C5B -38.5(2) . . . . ?
N1B C1B C2B C5B 143.30(13) . . . . ?
O1B C1B C2B C3B -165.92(16) . . . . ?
N1B C1B C2B C3B 15.87(16) . . . . ?
C5B C2B C3B C4B -142.10(13) . . . . ?
C1B C2B C3B C4B -16.16(16) . . . . ?
C1B N1B C4B O2B 179.75(14) . . . . ?
C1B N1B C4B C3B -1.41(17) . . . . ?
C2B C3B C4B O2B -169.73(15) . . . . ?
C2B C3B C4B N1B 11.49(16) . . . . ?
C1B C2B C5B C6B 141.55(15) . . . . ?
C3B C2B C5B C6B -98.08(18) . . . . ?
C1B C2B C5B C10B -39.0(2) . . . . ?
C3B C2B C5B C10B 81.42(19) . . . . ?
C10B C5B C6B C7B 1.4(2) . . . . ?
C2B C5B C6B C7B -179.14(15) . . . . ?
C5B C6B C7B C8B 0.8(3) . . . . ?
C6B C7B C8B C9B -1.9(3) . . . . ?
C7B C8B C9B C10B 0.9(3) . . . . ?
C8B C9B C10B C5B 1.3(3) . . . . ?
C6B C5B C10B C9B -2.4(3) . . . . ?
C2B C5B C10B C9B 178.10(17) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1A O2A 0.868(17) 1.967(17) 2.8346(18) 179.4(16) 2_655
N1B H1B O1A 0.914(19) 2.017(19) 2.9102(18) 165.4(16) .
_refine_diff_density_max 0.216
_refine_diff_density_min -0.181
_refine_diff_density_rms 0.036
_shelx_res_file
;
avk14a.res created by SHELXL-2014/7
TITL sad in P2(1)/c
CELL 0.71073 15.5636 5.7158 20.5949 90 107.363 90
ZERR 8 0.0051 0.0019 0.0077 0 0.006 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 80 72 8 16
EQIV $1 1-X, 0.5+Y, 0.5-Z
L.S. 4
PLAN 20
SIZE 0.1 0.1 0.2
TEMP -58
HTAB N1A O2A_$1
HTAB N1B O1A
BOND $H
CONF
fmap 2
acta
SHEL 100 0.755
REM
REM
REM
WGHT 0.039800 0.261000
FVAR 0.16167
O1A 4 0.609470 0.137384 0.156032 11.00000 0.03628 0.02794 =
0.04420 0.00250 0.00413 0.00443
O2A 4 0.587066 -0.525139 0.272233 11.00000 0.03378 0.03864 =
0.04110 0.00057 0.01255 -0.00909
N1A 3 0.583403 -0.170156 0.219246 11.00000 0.01931 0.03184 =
0.03314 -0.00381 0.00699 0.00254
H1A 2 0.531015 -0.126122 0.221544 11.00000 0.03437
C1A 1 0.633886 -0.042340 0.187864 11.00000 0.02463 0.02360 =
0.02998 -0.00671 0.00316 -0.00080
C2A 1 0.723907 -0.164825 0.199045 11.00000 0.02446 0.02323 =
0.04105 -0.00327 0.01211 -0.00159
H2A 2 0.730308 -0.195057 0.153471 11.00000 0.02981
C3A 1 0.712354 -0.393069 0.234189 11.00000 0.02710 0.02288 =
0.07131 0.00480 0.01703 0.00171
H3AA 2 0.757012 -0.418034 0.275053 11.00000 0.05490
H3AB 2 0.711984 -0.526001 0.205348 11.00000 0.05907
C4A 1 0.622424 -0.378494 0.245957 11.00000 0.02365 0.02794 =
0.02977 -0.00582 0.00508 -0.00464
C5A 1 0.799949 -0.006101 0.238112 11.00000 0.02066 0.02174 =
0.03542 0.00035 0.00759 0.00277
C6A 1 0.850612 0.113596 0.203822 11.00000 0.03035 0.03121 =
0.03706 -0.00074 0.01120 -0.00289
H6A 2 0.837868 0.092665 0.154388 11.00000 0.04370
C7A 1 0.918718 0.265126 0.238342 11.00000 0.03108 0.03702 =
0.05640 -0.00187 0.01582 -0.00991
H7A 2 0.953889 0.344085 0.213084 11.00000 0.05848
C8A 1 0.936919 0.296839 0.307030 11.00000 0.02908 0.03995 =
0.05557 -0.01142 0.00262 -0.00418
H8A 2 0.985489 0.401945 0.331041 11.00000 0.05483
C9A 1 0.887289 0.179248 0.341652 11.00000 0.03899 0.05698 =
0.03516 -0.00879 0.00315 0.00252
H9A 2 0.900753 0.202470 0.391128 11.00000 0.07178
C10A 1 0.818893 0.029059 0.307594 11.00000 0.03410 0.04494 =
0.03593 0.00219 0.01271 0.00044
H10A 2 0.781286 -0.048771 0.330288 11.00000 0.04428
O1B 4 0.340375 0.353595 0.118260 11.00000 0.04552 0.05081 =
0.04257 0.01798 0.01307 -0.00155
O2B 4 0.573007 0.671346 0.058193 11.00000 0.03155 0.04459 =
0.04429 -0.00534 0.00797 -0.00421
N1B 3 0.469558 0.481023 0.098243 11.00000 0.03259 0.03146 =
0.02953 0.00186 0.00190 0.00233
H1B 2 0.506108 0.361028 0.119306 11.00000 0.05312
C1B 1 0.381060 0.499769 0.096567 11.00000 0.03428 0.03671 =
0.02215 0.00037 0.00340 0.00034
C2B 1 0.346843 0.736049 0.065160 11.00000 0.03550 0.03066 =
0.02917 -0.00418 0.00518 0.00226
H2B 2 0.351597 0.838879 0.101994 11.00000 0.03234
C3B 1 0.417900 0.810878 0.031556 11.00000 0.03805 0.02809 =
0.04373 0.00395 0.01003 -0.00100
H3BA 2 0.435457 0.972970 0.037568 11.00000 0.04874
H3BB 2 0.398520 0.776835 -0.018116 11.00000 0.04863
C4B 1 0.497454 0.655662 0.062806 11.00000 0.03452 0.02940 =
0.02808 -0.00702 0.00392 -0.00414
C5B 1 0.250412 0.733082 0.020145 11.00000 0.03329 0.03339 =
0.03244 0.00740 0.00842 0.00113
C6B 1 0.194713 0.921038 0.021083 11.00000 0.04019 0.04158 =
0.04688 0.00898 0.01560 0.00522
H6B 2 0.218401 1.048524 0.051114 11.00000 0.05340
C7B 1 0.105496 0.919764 -0.019333 11.00000 0.03895 0.06359 =
0.06498 0.02624 0.01967 0.01252
H7B 2 0.067944 1.053198 -0.018187 11.00000 0.06427
C8B 1 0.071772 0.730148 -0.059882 11.00000 0.03553 0.07449 =
0.06079 0.03414 -0.00050 -0.00876
H8B 2 0.010633 0.727923 -0.086726 11.00000 0.07093
C9B 1 0.127089 0.545067 -0.061900 11.00000 0.05996 0.05171 =
0.05383 0.01497 -0.01426 -0.01357
H9B 2 0.105315 0.416939 -0.090599 11.00000 0.07622
C10B 1 0.216503 0.546208 -0.022668 11.00000 0.05237 0.03824 =
0.04382 0.00319 -0.00550 0.00006
H10B 2 0.255536 0.413221 -0.025318 11.00000 0.06441
HKLF 4
REM sad in P2(1)/c
REM R1 = 0.0429 for 2869 Fo > 4sig(Fo) and 0.0757 for all 4257 data
REM 307 parameters refined using 0 restraints
END
WGHT 0.0397 0.2615
REM Highest difference peak 0.216, deepest hole -0.181, 1-sigma level 0.036
Q1 1 0.7600 -0.0846 0.2211 11.00000 0.05 0.22
Q2 1 0.6845 -0.0964 0.1961 11.00000 0.05 0.21
Q3 1 0.8094 0.1099 0.2230 11.00000 0.05 0.19
Q4 1 0.3004 0.7406 0.0379 11.00000 0.05 0.18
Q5 1 0.7138 -0.2798 0.2111 11.00000 0.05 0.16
Q6 1 0.5897 0.8417 0.0612 11.00000 0.05 0.15
Q7 1 0.9042 0.1351 0.2244 11.00000 0.05 0.15
Q8 1 0.7976 0.0456 0.2689 11.00000 0.05 0.15
Q9 1 0.8630 0.2697 0.2204 11.00000 0.05 0.15
Q10 1 0.2515 0.6708 -0.0129 11.00000 0.05 0.14
Q11 1 0.2421 0.8583 0.0088 11.00000 0.05 0.14
Q12 1 0.9219 0.1965 0.3223 11.00000 0.05 0.13
Q13 1 0.6540 -0.4222 0.2186 11.00000 0.05 0.13
Q14 1 0.8295 0.1619 0.3241 11.00000 0.05 0.13
Q15 1 0.2671 0.3571 0.0993 11.00000 0.05 0.13
Q16 1 0.4518 0.6903 0.0404 11.00000 0.05 0.13
Q17 1 0.6057 0.5387 0.0760 11.00000 0.05 0.13
Q18 1 0.5474 0.5302 0.0410 11.00000 0.05 0.13
Q19 1 0.7255 -0.1844 0.1785 11.00000 0.05 0.13
Q20 1 0.3139 0.8943 0.1599 11.00000 0.05 0.13
;
_shelx_res_checksum 1446
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexanes/acetone (2:1)'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_PII_175K
_database_code_depnum_ccdc_archive 'CCDC 1957489'
loop_
_audit_author_name
_audit_author_address
'Tatiana Timofeeva'
;New Mexico Highlands University
United States of America
;
_audit_update_record
;
2019-10-03 deposited with the CCDC. 2019-10-14 downloaded from the CCDC.
;
_audit_creation_date 2019-08-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2017/1
_chemical_name_common ?
_chemical_name_systematic rac-3-phenylpyrrolidin-2,5-dione
_chemical_formula_moiety 'C10 H9 N O2'
_chemical_formula_sum 'C10 H9 N O2'
_chemical_formula_weight 175.18
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 15.575(6)
_cell_length_b 5.711(2)
_cell_length_c 20.567(8)
_cell_angle_alpha 90
_cell_angle_beta 107.533(5)
_cell_angle_gamma 90
_cell_volume 1744.5(12)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 3740
_cell_measurement_temperature 175
_cell_measurement_theta_max 23.852
_cell_measurement_theta_min 3.716
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.094
_exptl_absorpt_correction_T_max 0.7450
_exptl_absorpt_correction_T_min 0.6463
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0642 before and 0.0470 after correction. The Ratio of minimum to maximum transmission is 0.8675. The \l/2 correction factor is 0.0015.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.334
_exptl_crystal_density_meas .
_exptl_crystal_density_method ?
_exptl_crystal_description plate
_exptl_crystal_F_000 736
_exptl_crystal_preparation ?
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max 0.2
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.1
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0516
_diffrn_reflns_av_unetI/netI 0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_k_max 6
_diffrn_reflns_limit_k_min -6
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_number 15783
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full 24.116
_diffrn_reflns_theta_max 24.116
_diffrn_reflns_theta_min 2.743
_diffrn_ambient_temperature 175
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type 'Bruker APEX-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_diffrn_special_details ?
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2158
_reflns_number_total 2756
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement 'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection ?
_computing_data_reduction 'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'XL (Sheldrick, 2008)'
_computing_structure_solution 'XS (Sheldrick, 2008)'
_refine_diff_density_max 0.177
_refine_diff_density_min -0.205
_refine_diff_density_rms 0.052
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.025
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 243
_refine_ls_number_reflns 2756
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0497
_refine_ls_R_factor_gt 0.0331
_refine_ls_restrained_S_all 1.025
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.2338P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0773
_refine_ls_wR_factor_ref 0.0850
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
C3(H3), C3A(H3A)
2.b Secondary CH2 refined with riding coordinates:
C2(H2A,H2B), C2A(H2AA,H2AB)
2.c Aromatic/amide H refined with riding coordinates:
C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C6A(H6A), C7A(H7A), C8A(H8A),
C9A(H9A), C10A(H10A)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.57284(7) 0.6714(2) 0.05841(5) 0.0413(3) Uani 1 1 d . . . . .
O2 O 0.34015(8) 0.3537(2) 0.11813(6) 0.0466(3) Uani 1 1 d . . . . .
N1 N 0.46906(9) 0.4815(2) 0.09822(6) 0.0326(3) Uani 1 1 d . . . . .
C1 C 0.49715(11) 0.6555(3) 0.06282(7) 0.0319(4) Uani 1 1 d . . . . .
C2 C 0.41782(10) 0.8103(3) 0.03121(8) 0.0378(4) Uani 1 1 d . . . . .
H2A H 0.395418 0.786386 -0.018750 0.045 Uiso 1 1 calc R . . . .
H2B H 0.434032 0.977260 0.040517 0.045 Uiso 1 1 calc R . . . .
C3 C 0.34666(10) 0.7361(3) 0.06503(8) 0.0354(4) Uani 1 1 d . . . . .
H3 H 0.350275 0.847652 0.103235 0.042 Uiso 1 1 calc R . . . .
C4 C 0.38073(11) 0.4998(3) 0.09636(7) 0.0329(4) Uani 1 1 d . . . . .
C5 C 0.25033(10) 0.7329(3) 0.01977(8) 0.0338(4) Uani 1 1 d . . . . .
C6 C 0.19465(11) 0.9211(3) 0.02099(9) 0.0435(4) Uani 1 1 d . . . . .
H6 H 0.217630 1.051313 0.049684 0.052 Uiso 1 1 calc R . . . .
C7 C 0.10541(12) 0.9201(4) -0.01955(10) 0.0547(5) Uani 1 1 d . . . . .
H7 H 0.067816 1.050916 -0.019324 0.066 Uiso 1 1 calc R . . . .
C8 C 0.07168(13) 0.7301(4) -0.05987(10) 0.0598(6) Uani 1 1 d . . . . .
H8 H 0.010024 0.726517 -0.086197 0.072 Uiso 1 1 calc R . . . .
C9 C 0.12704(14) 0.5446(4) -0.06226(10) 0.0625(6) Uani 1 1 d . . . . .
H9 H 0.103912 0.414811 -0.091085 0.075 Uiso 1 1 calc R . . . .
C10 C 0.21585(13) 0.5470(3) -0.02295(9) 0.0502(5) Uani 1 1 d . . . . .
H10 H 0.253855 0.419120 -0.025241 0.060 Uiso 1 1 calc R . . . .
O1A O 0.58702(7) -0.52561(19) 0.27233(5) 0.0376(3) Uani 1 1 d . . . . .
O2A O 0.60940(7) 0.13790(18) 0.15604(5) 0.0382(3) Uani 1 1 d . . . . .
N1A N 0.58338(9) -0.1702(2) 0.21925(6) 0.0291(3) Uani 1 1 d . . . . .
C1A C 0.62243(10) -0.3788(3) 0.24607(7) 0.0289(4) Uani 1 1 d . . . . .
C2A C 0.71242(10) -0.3935(3) 0.23465(10) 0.0397(4) Uani 1 1 d . . . . .
H2AA H 0.714988 -0.529591 0.205493 0.048 Uiso 1 1 calc R . . . .
H2AB H 0.760574 -0.409960 0.278602 0.048 Uiso 1 1 calc R . . . .
C3A C 0.72379(9) -0.1642(2) 0.19920(8) 0.0297(4) Uani 1 1 d . . . . .
H3A H 0.731755 -0.201726 0.153881 0.036 Uiso 1 1 calc R . . . .
C4A C 0.63395(10) -0.0423(3) 0.18797(7) 0.0280(3) Uani 1 1 d . . . . .
C5A C 0.79992(9) -0.0063(2) 0.23819(7) 0.0274(3) Uani 1 1 d . . . . .
C6A C 0.81875(11) 0.0297(3) 0.30767(8) 0.0387(4) Uani 1 1 d . . . . .
H6A H 0.784525 -0.049386 0.332112 0.046 Uiso 1 1 calc R . . . .
C7A C 0.88712(11) 0.1803(3) 0.34168(9) 0.0451(4) Uani 1 1 d . . . . .
H7A H 0.899736 0.202886 0.389401 0.054 Uiso 1 1 calc R . . . .
C8A C 0.93685(11) 0.2974(3) 0.30722(9) 0.0432(4) Uani 1 1 d . . . . .
H8A H 0.983661 0.400574 0.330904 0.052 Uiso 1 1 calc R . . . .
C9A C 0.91859(11) 0.2645(3) 0.23844(9) 0.0412(4) Uani 1 1 d . . . . .
H9A H 0.952856 0.345340 0.214371 0.049 Uiso 1 1 calc R . . . .
C10A C 0.85046(10) 0.1140(3) 0.20378(8) 0.0334(4) Uani 1 1 d . . . . .
H10A H 0.838183 0.092865 0.156024 0.040 Uiso 1 1 calc R . . . .
H1A H 0.5319(12) -0.126(3) 0.2225(8) 0.044(5) Uiso 1 1 d . . . . .
H1 H 0.5039(12) 0.366(3) 0.1178(8) 0.043(5) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0342(7) 0.0434(7) 0.0441(7) -0.0061(5) 0.0084(5) -0.0051(5)
O2 0.0469(7) 0.0502(8) 0.0429(7) 0.0169(6) 0.0137(6) -0.0009(6)
N1 0.0352(8) 0.0283(7) 0.0294(7) 0.0027(6) 0.0026(6) 0.0035(6)
C1 0.0345(9) 0.0281(8) 0.0299(8) -0.0070(7) 0.0048(7) -0.0036(7)
C2 0.0389(9) 0.0285(8) 0.0438(10) 0.0050(7) 0.0091(8) -0.0008(7)
C3 0.0382(9) 0.0317(9) 0.0332(9) -0.0037(7) 0.0063(7) 0.0027(7)
C4 0.0360(10) 0.0348(9) 0.0252(8) 0.0007(7) 0.0051(7) 0.0009(7)
C5 0.0356(9) 0.0308(9) 0.0342(9) 0.0078(7) 0.0092(7) 0.0013(7)
C6 0.0436(11) 0.0387(10) 0.0502(11) 0.0081(8) 0.0169(8) 0.0035(8)
C7 0.0408(11) 0.0623(13) 0.0627(12) 0.0263(11) 0.0182(9) 0.0125(10)
C8 0.0381(10) 0.0705(15) 0.0612(13) 0.0329(12) 0.0006(9) -0.0081(11)
C9 0.0643(14) 0.0507(12) 0.0534(12) 0.0150(10) -0.0110(10) -0.0136(11)
C10 0.0548(12) 0.0382(10) 0.0450(10) 0.0033(9) -0.0037(9) 0.0001(9)
O1A 0.0356(6) 0.0370(6) 0.0407(6) 0.0007(5) 0.0121(5) -0.0084(5)
O2A 0.0383(6) 0.0274(6) 0.0443(7) 0.0023(5) 0.0056(5) 0.0040(5)
N1A 0.0221(7) 0.0308(7) 0.0337(7) -0.0032(6) 0.0074(6) 0.0027(6)
C1A 0.0278(8) 0.0263(8) 0.0296(8) -0.0053(7) 0.0040(7) -0.0047(7)
C2A 0.0287(9) 0.0226(8) 0.0690(12) 0.0018(8) 0.0163(8) -0.0005(7)
C3A 0.0260(8) 0.0228(8) 0.0419(9) -0.0033(7) 0.0127(7) -0.0006(6)
C4A 0.0274(8) 0.0240(8) 0.0296(8) -0.0073(7) 0.0040(6) -0.0029(7)
C5A 0.0237(8) 0.0215(7) 0.0366(9) 0.0012(6) 0.0084(6) 0.0034(6)
C6A 0.0363(9) 0.0428(10) 0.0385(10) 0.0024(8) 0.0137(7) -0.0001(8)
C7A 0.0400(10) 0.0542(11) 0.0360(9) -0.0090(8) 0.0038(8) 0.0023(9)
C8A 0.0309(9) 0.0381(10) 0.0544(11) -0.0117(8) 0.0033(8) -0.0038(8)
C9A 0.0327(9) 0.0366(10) 0.0557(11) -0.0003(8) 0.0152(8) -0.0097(8)
C10A 0.0329(9) 0.0313(9) 0.0369(9) -0.0015(7) 0.0119(7) -0.0031(7)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2126(19) . ?
O2 C4 1.2110(19) . ?
N1 C1 1.379(2) . ?
N1 C4 1.369(2) . ?
C1 C2 1.499(2) . ?
C2 C3 1.535(2) . ?
C3 C4 1.521(2) . ?
C3 C5 1.509(2) . ?
C5 C6 1.386(2) . ?
C5 C10 1.380(2) . ?
C6 C7 1.389(3) . ?
C7 C8 1.371(3) . ?
C8 C9 1.376(3) . ?
C9 C10 1.376(3) . ?
O1A C1A 1.2159(18) . ?
O2A C4A 1.2190(18) . ?
N1A C1A 1.375(2) . ?
N1A C4A 1.369(2) . ?
C1A C2A 1.492(2) . ?
C2A C3A 1.535(2) . ?
C3A C4A 1.517(2) . ?
C3A C5A 1.513(2) . ?
C5A C6A 1.385(2) . ?
C5A C10A 1.389(2) . ?
C6A C7A 1.384(2) . ?
C7A C8A 1.371(2) . ?
C8A C9A 1.369(2) . ?
C9A C10A 1.384(2) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C1 113.98(14) . . ?
O1 C1 N1 124.32(14) . . ?
O1 C1 C2 128.03(15) . . ?
N1 C1 C2 107.64(14) . . ?
C1 C2 C3 104.70(13) . . ?
C4 C3 C2 103.28(13) . . ?
C5 C3 C2 116.31(13) . . ?
C5 C3 C4 113.96(13) . . ?
O2 C4 N1 124.70(15) . . ?
O2 C4 C3 127.86(15) . . ?
N1 C4 C3 107.40(14) . . ?
C6 C5 C3 119.40(15) . . ?
C10 C5 C3 121.73(15) . . ?
C10 C5 C6 118.87(16) . . ?
C5 C6 C7 120.31(18) . . ?
C8 C7 C6 119.88(19) . . ?
C7 C8 C9 120.06(18) . . ?
C10 C9 C8 120.09(19) . . ?
C9 C10 C5 120.73(18) . . ?
C4A N1A C1A 113.77(13) . . ?
O1A C1A N1A 124.78(14) . . ?
O1A C1A C2A 127.21(14) . . ?
N1A C1A C2A 107.97(13) . . ?
C1A C2A C3A 105.98(12) . . ?
C4A C3A C2A 103.34(12) . . ?
C5A C3A C2A 116.16(13) . . ?
C5A C3A C4A 110.31(12) . . ?
O2A C4A N1A 124.92(14) . . ?
O2A C4A C3A 126.49(14) . . ?
N1A C4A C3A 108.59(13) . . ?
C6A C5A C3A 121.60(13) . . ?
C6A C5A C10A 118.43(14) . . ?
C10A C5A C3A 119.92(14) . . ?
C7A C6A C5A 120.37(15) . . ?
C8A C7A C6A 120.69(16) . . ?
C9A C8A C7A 119.56(16) . . ?
C8A C9A C10A 120.37(15) . . ?
C9A C10A C5A 120.58(15) . . ?
_shelx_res_file
;
TITL avk14f3 in P21/c #14
avk14f3.res
created by SHELXL-2017/1 at 13:13:10 on 06-Aug-2019
REM reset to P21/c #14
CELL 0.71073 15.5751 5.7113 20.5672 90 107.533 90
ZERR 8 0.0061 0.0022 0.0081 0 0.005 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 80 72 8 16
L.S. 25
PLAN 9
TEMP -173
BOND
fmap 2
acta
OMIT -2 1 1
OMIT 1 0 0
OMIT -2 1 2
OMIT -3 0 2
OMIT 1 1 0
OMIT -3 1 3
OMIT 2 0 2
OMIT 1 0 4
OMIT 0 1 1
OMIT -1 0 2
OMIT 2 1 0
REM
REM
REM
WGHT 0.043000 0.233800
FVAR 0.16535
O1 4 0.572835 0.671442 0.058412 11.00000 0.03420 0.04338 =
0.04406 -0.00607 0.00843 -0.00506
O2 4 0.340153 0.353704 0.118130 11.00000 0.04689 0.05020 =
0.04288 0.01686 0.01373 -0.00087
N1 3 0.469064 0.481497 0.098218 11.00000 0.03520 0.02832 =
0.02942 0.00270 0.00263 0.00349
C1 1 0.497149 0.655495 0.062817 11.00000 0.03451 0.02814 =
0.02986 -0.00705 0.00484 -0.00364
C2 1 0.417818 0.810345 0.031206 11.00000 0.03892 0.02848 =
0.04380 0.00505 0.00911 -0.00079
AFIX 23
H2A 2 0.395418 0.786386 -0.018750 11.00000 -1.20000
H2B 2 0.434032 0.977260 0.040517 11.00000 -1.20000
AFIX 0
C3 1 0.346656 0.736094 0.065026 11.00000 0.03824 0.03175 =
0.03321 -0.00367 0.00630 0.00268
AFIX 13
H3 2 0.350275 0.847652 0.103235 11.00000 -1.20000
AFIX 0
C4 1 0.380732 0.499772 0.096359 11.00000 0.03604 0.03477 =
0.02521 0.00067 0.00514 0.00093
C5 1 0.250327 0.732928 0.019768 11.00000 0.03557 0.03081 =
0.03417 0.00784 0.00919 0.00126
C6 1 0.194647 0.921073 0.020986 11.00000 0.04355 0.03866 =
0.05021 0.00808 0.01689 0.00349
AFIX 43
H6 2 0.217630 1.051313 0.049684 11.00000 -1.20000
AFIX 0
C7 1 0.105412 0.920125 -0.019546 11.00000 0.04075 0.06227 =
0.06273 0.02635 0.01823 0.01245
AFIX 43
H7 2 0.067816 1.050916 -0.019324 11.00000 -1.20000
AFIX 0
C8 1 0.071680 0.730144 -0.059870 11.00000 0.03813 0.07053 =
0.06115 0.03288 0.00065 -0.00809
AFIX 43
H8 2 0.010024 0.726517 -0.086197 11.00000 -1.20000
AFIX 0
C9 1 0.127042 0.544647 -0.062257 11.00000 0.06432 0.05069 =
0.05345 0.01498 -0.01099 -0.01362
AFIX 43
H9 2 0.103912 0.414811 -0.091085 11.00000 -1.20000
AFIX 0
C10 1 0.215854 0.546965 -0.022947 11.00000 0.05481 0.03824 =
0.04504 0.00331 -0.00372 0.00013
AFIX 43
H10 2 0.253855 0.419120 -0.025241 11.00000 -1.20000
AFIX 0
O1A 4 0.587023 -0.525608 0.272332 11.00000 0.03558 0.03704 =
0.04068 0.00066 0.01207 -0.00841
O2A 4 0.609399 0.137895 0.156039 11.00000 0.03835 0.02745 =
0.04433 0.00233 0.00557 0.00397
N1A 3 0.583376 -0.170212 0.219253 11.00000 0.02214 0.03077 =
0.03371 -0.00321 0.00740 0.00272
C1A 1 0.622433 -0.378801 0.246072 11.00000 0.02781 0.02629 =
0.02956 -0.00527 0.00403 -0.00468
C2A 1 0.712419 -0.393465 0.234649 11.00000 0.02867 0.02259 =
0.06898 0.00177 0.01635 -0.00048
AFIX 23
H2AA 2 0.714988 -0.529591 0.205493 11.00000 -1.20000
H2AB 2 0.760574 -0.409960 0.278602 11.00000 -1.20000
AFIX 0
C3A 1 0.723787 -0.164180 0.199204 11.00000 0.02603 0.02284 =
0.04191 -0.00335 0.01273 -0.00058
AFIX 13
H3A 2 0.731755 -0.201726 0.153881 11.00000 -1.20000
AFIX 0
C4A 1 0.633949 -0.042332 0.187975 11.00000 0.02743 0.02403 =
0.02964 -0.00733 0.00402 -0.00294
C5A 1 0.799924 -0.006313 0.238193 11.00000 0.02367 0.02150 =
0.03663 0.00120 0.00835 0.00340
C6A 1 0.818747 0.029731 0.307667 11.00000 0.03630 0.04280 =
0.03847 0.00243 0.01365 -0.00005
AFIX 43
H6A 2 0.784525 -0.049386 0.332112 11.00000 -1.20000
AFIX 0
C7A 1 0.887118 0.180333 0.341675 11.00000 0.04001 0.05416 =
0.03596 -0.00903 0.00383 0.00230
AFIX 43
H7A 2 0.899736 0.202886 0.389401 11.00000 -1.20000
AFIX 0
C8A 1 0.936845 0.297352 0.307219 11.00000 0.03087 0.03808 =
0.05435 -0.01168 0.00331 -0.00376
AFIX 43
H8A 2 0.983661 0.400574 0.330904 11.00000 -1.20000
AFIX 0
C9A 1 0.918587 0.264461 0.238439 11.00000 0.03266 0.03658 =
0.05570 -0.00029 0.01517 -0.00973
AFIX 43
H9A 2 0.952856 0.345340 0.214371 11.00000 -1.20000
AFIX 0
C10A 1 0.850463 0.113996 0.203775 11.00000 0.03294 0.03131 =
0.03687 -0.00146 0.01187 -0.00311
AFIX 43
H10A 2 0.838183 0.092865 0.156024 11.00000 -1.20000
AFIX 0
H1A 2 0.531885 -0.126107 0.222547 11.00000 0.04410
H1 2 0.503923 0.365631 0.117828 11.00000 0.04302
HKLF 4
REM avk14f3 in P21/c #14
REM R1 = 0.0331 for 2158 Fo > 4sig(Fo) and 0.0497 for all 2756 data
REM 243 parameters refined using 0 restraints
END
WGHT 0.0429 0.2335
REM Highest difference peak 0.177, deepest hole -0.205, 1-sigma level 0.052
Q1 1 0.7458 -0.7550 0.2238 11.00000 0.05 0.18
Q2 1 0.7847 -0.5734 0.2528 11.00000 0.05 0.17
Q3 1 0.7628 0.1709 0.1809 11.00000 0.05 0.17
Q4 1 0.7640 0.2814 0.2796 11.00000 0.05 0.16
Q5 1 0.4091 0.3084 0.1673 11.00000 0.05 0.16
Q6 1 0.5850 -0.2896 0.2227 11.00000 0.05 0.16
Q7 1 0.3299 0.5830 0.0117 11.00000 0.05 0.16
Q8 1 0.5814 0.7550 0.1305 11.00000 0.05 0.16
Q9 1 0.8002 0.1229 0.2182 11.00000 0.05 0.16
;
_shelx_res_checksum 48809
_olex2_submission_original_sample_id AVK14F3
_olex2_submission_special_instructions 'No special instructions were received'